[ CAS No. 79-39-0 ] {[proInfo.proName]}

Name: 79-39-0|Methacrylamide|98%
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2D 3D

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Quality Control of [ 79-39-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 79-39-0 ]

SDS Specification

Alternatived Products of [ 79-39-0 ]

Product Details of [ 79-39-0 ]

CAS No. :	79-39-0	MDL No. :	MFCD00008018
Formula :	C₄H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FQPSGWSUVKBHSU-UHFFFAOYSA-N
M.W :	85.10	Pubchem ID :	6595
Synonyms :	2-Methylacrylamide

Calculated chemistry of [ 79-39-0 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	23.78
TPSA :	43.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.99
Log Po/w (XLOGP3) :	-1.11
Log Po/w (WLOGP) :	0.05
Log Po/w (MLOGP) :	-0.03
Log Po/w (SILICOS-IT) :	-0.27
Consensus Log Po/w :	-0.07

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.4
Solubility :	213.0 mg/ml ; 2.5 mol/l
Class :	Highly soluble
Log S (Ali) :	0.7
Solubility :	422.0 mg/ml ; 4.96 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.2
Solubility :	54.3 mg/ml ; 0.638 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 79-39-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 79-39-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 79-39-0 ]
Downstream synthetic route of [ 79-39-0 ]

[ 79-39-0 ] Synthesis Path-Upstream 1~3

1
[ 109-75-1 ]
[ 461-98-3 ]
[ 541-35-5 ]
[ 64-17-5 ]
[ 79-39-0 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 33, p. 6301 - 6304

2
[ 75-86-5 ]
[ 49562-37-0 ]
[ 13027-88-8 ]
[ 79-39-0 ]

Reference： [1] Patent: US2006/111586, 2006, A1, . Location in patent: Page/Page column 5-6; 8
[2] Patent: US2006/111586, 2006, A1, . Location in patent: Page/Page column 6-8

3
[ 79-39-0 ]
[ 194853-86-6 ]
[ 90357-53-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride In hexane; water; N,N-dimethyl-formamide	EXAMPLE 1 Preparation of N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide To a solution of methacrylamide (153.00 g, 1797.88 mmol) in 800 mL of N,N-dimethylformamide was added 4-cyano-3-(trifluoromethyl)phenyl fluoride (200 g, 1057.58 mmol) at room temperature. The solution was cooled in a methanol/dry ice bath to -20° C. To this cooled solution was added sodium hydride (102 g, 2696.84 mmol), portion-wise, while keeping the reaction mixture temperature below 70° C. The reaction mixture was allowed to cool to room temperature and stirred for 4 hours under nitrogen atmosphere. Water (915 mL) was added followed by 18percent HCl (250 mL) and hexane (970 mL). The resultant slurry was allowed to stir overnight. The solid was filtered, washed sequentially with water (3*150 mL) and hexane (100 mL), and dried at 60° C. to give the title product as an off white solid (260 g, 97percent). ¹H NMR (CDCl₃) δ 7.87 (d, J=1.9 Hz, 111), 7.80 (dd, J=1.9, 8.5 Hz, 1H), 7.69 (bs, 1H), 7.62 (d, J=8.5 Hz, 1H), 5.69 (s, 1H), 5.44 (t, J=1.5 Hz, 1H), 1.90 (s, 3H).

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10181 - 10182
[2] Patent: US2002/86902, 2002, A1,
[3] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1049 - 1056

[ 79-39-0 ] Synthesis Path-Downstream 1~88

1
[ 625-51-4 ]
[ 107-06-2 ]
[ 79-39-0 ]
[ 98336-87-9 ]

Reference： [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 3943; engl. Ausg. S. 3902

2
[ 79-39-0 ]
[ 100-63-0 ]
[ 2654-57-1 ]

Reference： [1]Patent: US2704762,1953,

3
[ 79-39-0 ]
[ 126-98-7 ]

Yield	Reaction Conditions	Operation in experiment
94.7%	With polyionic liquid acid binding agent; In acetonitrile; at 80℃; for 10h;Inert atmosphere;	According to parts by mass, 150 parts of (meth) acrylamide was dissolved in 1500 parts of organic solution, stirred and mixed uniformly, and then 5 parts of polyionic liquid acid binding agent was added to the reaction kettle, under the protection of nitrogen, The temperature was controlled at 80 C, and the reaction was carried out for 10 hours. After the reaction was completed, further catalytic dehydration treatment was performed. After the dehydration reaction was completed, the product was rectified to obtain the product (meth) acrylonitrile.The catalytic reaction bed has a reaction temperature of 300 C and a residence time of 5 seconds.The organic solvent is acetonitrile.

Reference： [1]Patent: CN110511160,2019,A .Location in patent: Paragraph 0025-0093
[2]Organometallics,2015,vol. 34,p. 1228 - 1237
[3]Journal of the American Chemical Society,1947,vol. 69,p. 1831

4
[ 126-98-7 ]
[ 79-39-0 ]

Yield	Reaction Conditions	Operation in experiment
>99%	With RuCl2(eta6-p-cymene){PPh2(OH)}; water; In ethanol; at 80℃;Inert atmosphere; Sealed tube;	General procedure: Examples 9-1 to 9-8 (0114) The results obtained by carrying out catalytic hydration reactions of various nitriles using the complex B are set forth in Table 9. In a screw-top glass test tube, the complex A (0.005 mmol Ru), a given amount of a ligand, acrylonitrile (67 muL, 1 mmol), water (72 muL, 4 mmol) and 0.5 mL of a given solvent were placed in an argon atmosphere, and the test tube was closed. Then, the test tube was heated at 80 C. for a given period of time. The yield of acrylamide was calculated by a gas chromatograph

Reference： [1]Dalton Transactions,2015,vol. 44,p. 12082 - 12085
[2]Patent: US8722912,2014,B2 .Location in patent: Page/Page column 27
[3]Angewandte Chemie - International Edition,2008,vol. 47,p. 3607 - 3609
[4]Journal of the Korean Chemical Society,2011,vol. 55,p. 715 - 718
[5]Bulletin de la Classe des Sciences, Academie Royale de Belgique,1927,vol. <5> 13,p. 767,776
Chemisches Zentralblatt,1928,vol. 99,p. 1644
[6]ChemSusChem,2012,vol. 5,p. 1392 - 1396
[7]Organometallics,2013,vol. 32,p. 3744 - 3752

5
[ 6304-16-1 ]
[ 79-39-0 ]
[ 89733-50-6 ]

Reference： [1]Synthesis,1985,p. 305 - 306

6
[ 108-98-5 ]
[ 79-39-0 ]
[ 22437-44-1 ]

Reference： [1]RSC Advances,2017,vol. 7,p. 43104 - 43113
[2]Synthetic Communications,2005,vol. 35,p. 2427 - 2433
[3]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 2225 - 2232

7
[ 3017-69-4 ]
[ 79-39-0 ]
[ 76232-52-5 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 1067 - 1073

8
[ 5350-57-2 ]
[ 79-39-0 ]
[ 86456-50-0 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 2968 - 2972

9
[ 79-39-0 ]
[ 529-34-0 ]
[ 97110-07-1 ]

Reference： [1]Tetrahedron Letters,1985,vol. 26,p. 1311 - 1314
[2]Tetrahedron Letters,2001,vol. 42,p. 261 - 263
[3]Tetrahedron,2004,vol. 60,p. 4197 - 4204

10
[ 79-39-0 ]
[ 79-31-2 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 1941 - 1942

11
[ 97-90-5 ]
[ 79-39-0 ]
polymer, molecularly imprinted polymer, methotrexate used as template; monomer(s): methacrylamide; ethylene glycol dimethacrylate, cross-linking monomer [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 2146 - 2154

12
[ 97-90-5 ]
[ 79-39-0 ]
polymer; monomer(s): methacrylamide; ethylene glycol dimethacrylate, cross-linking monomer [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 2146 - 2154

13
[ 5536-61-8 ]
[ 79-39-0 ]
polymer; monomer(s): methacrylamide; sodium methacrylate [ No CAS ]

Reference： [1]Russian Journal of Applied Chemistry,2001,vol. 74,p. 2073 - 2078

14
[ 79-39-0 ]
[ 412272-46-9 ]
4-(2-iodophenyl)-2-methyl-4-(p-toluenesulfonyl)butanamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 5216 - 5225

15
[ 3839-31-4 ]
[ 79-39-0 ]
3-(dimethyl(phenyl)silyl)-2-methylpropionamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 580 - 589

16
[ 109-75-1 ]
[ 461-98-3 ]
[ 541-35-5 ]
[ 64-17-5 ]
[ 79-39-0 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 6301 - 6304

17
[ 97-90-5 ]
[ 79-39-0 ]
polyethylene dimethacrylate - polymetacrylamide copolymer, 90 percent:10 percent; monomer(s): ethylene dimethacrylate; methacrylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 9048 - 9054

18
[ 97-90-5 ]
[ 79-39-0 ]
polyethylene dimethacrylate - polymetacrylamide copolymer, 95 percent:5 percent; monomer(s): ethylene dimethacrylate; methacrylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 9048 - 9054

19
[ 97-90-5 ]
[ 79-39-0 ]
polyethylene dimethacrylate - polymetacrylamide copolymer, 85 percent:15 percent; monomer(s): ethylene dimethacrylate; methacrylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 9048 - 9054

20
[ 97-90-5 ]
[ 79-39-0 ]
polyethylene dimethacrylate - polymetacrylamide copolymer, 80 percent:20 percent; monomer(s): ethylene dimethacrylate; methacrylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 9048 - 9054

21
[ 97-90-5 ]
[ 79-39-0 ]
polyethylene dimethacrylate - polymetacrylamide copolymer, 75 percent:25 percent; monomer(s): ethylene dimethacrylate; methacrylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 9048 - 9054

22
[ 79-39-0 ]
[ 185999-05-7 ]
11-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-methyl-undec-2-enoic acid amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11360 - 11370

23
[ 70-23-5 ]
[ 79-39-0 ]
[ 618884-46-1 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 4421 - 4424

24
[ 79-39-0 ]
[ 194853-86-6 ]
[ 90357-53-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride; In hexane; water; N,N-dimethyl-formamide;	EXAMPLE 1 Preparation of N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide To a solution of methacrylamide (153.00 g, 1797.88 mmol) in 800 mL of N,N-dimethylformamide was added <strong>[194853-86-6]4-cyano-3-(trifluoromethyl)phenyl fluoride</strong> (200 g, 1057.58 mmol) at room temperature. The solution was cooled in a methanol/dry ice bath to -20 C. To this cooled solution was added sodium hydride (102 g, 2696.84 mmol), portion-wise, while keeping the reaction mixture temperature below 70 C. The reaction mixture was allowed to cool to room temperature and stirred for 4 hours under nitrogen atmosphere. Water (915 mL) was added followed by 18% HCl (250 mL) and hexane (970 mL). The resultant slurry was allowed to stir overnight. The solid was filtered, washed sequentially with water (3*150 mL) and hexane (100 mL), and dried at 60 C. to give the title product as an off white solid (260 g, 97%). 1H NMR (CDCl3) delta 7.87 (d, J=1.9 Hz, 111), 7.80 (dd, J=1.9, 8.5 Hz, 1H), 7.69 (bs, 1H), 7.62 (d, J=8.5 Hz, 1H), 5.69 (s, 1H), 5.44 (t, J=1.5 Hz, 1H), 1.90 (s, 3H).

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 10181 - 10182
[2]Patent: US2002/86902,2002,A1
[3]Journal of Organometallic Chemistry,2011,vol. 696,p. 1049 - 1056

25
[ 501-53-1 ]
[ 79-39-0 ]
[ 102254-14-8 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 1861 - 1864

26
[ 19115-30-1 ]
[ 79-39-0 ]
2-isopropenyl-5-(4-methoxyphenyl)-4-methyloxazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 4951 - 4955

27
potassium D-glucose-6-O-sulfate [ No CAS ]
[ 13749-61-6 ]
[ 97-90-5 ]
[ 79-39-0 ]
polymer, free-radical polymerization; monomer(s): potassium D-glucose-6-O-sulfate; N-isopropylmethacrylamide; methacrylamide; ethylene glycol dimethacrylate [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 1857 - 1862

28
[ 13749-61-6 ]
[ 97-90-5 ]
[ 79-39-0 ]
polymer, free-radical polymerization; monomer(s): N-isopropylmethacrylamide; methacrylamide; ethylene glycol dimethacrylate [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 1857 - 1862

29
potassium D-glucose-6-O-sulfate [ No CAS ]
[ 97-90-5 ]
[ 7659-36-1 ]
[ 79-39-0 ]
polymer, free-radical polymerization; monomer(s): potassium D-glucose-6-O-sulfate; 2-aminoethyl methacrylate; methacrylamide; ethylene glycol dimethacrylate [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 1857 - 1862
[2]Tetrahedron,2007,vol. 63,p. 1857 - 1862
[3]Tetrahedron,2007,vol. 63,p. 1857 - 1862

30
[ 97-90-5 ]
[ 7659-36-1 ]
[ 79-39-0 ]
polymer, free-radical polymerization; monomer(s): 2-aminoethyl methacrylate; methacrylamide; ethylene glycol dimethacrylate [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 1857 - 1862
[2]Tetrahedron,2007,vol. 63,p. 1857 - 1862

31
[ 3839-31-4 ]
[ 79-39-0 ]
3-(dimethyl(phenyl)silyl)-2-methylpropionamide [ No CAS ]

Reference： [1]Chemical Communications,2003,p. 144 - 145

32
[ 79-39-0 ]
[ 140-88-5 ]
N-[ethoxy (Z)-propenoyl]-2-methyl-2-propenonamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 12954 - 12962

33
[ 2680-03-7 ]
[ 79-39-0 ]
N-[N',N'-dimethylamino-(Z)-propenoyl]-2-methyl-2-propenonamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 12954 - 12962

34
[ 682-30-4 ]
[ 79-39-0 ]
N-[2-diethylphosphoryl-(Z)-ethenyl]-2-methyl-2-propenonamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 12954 - 12962

35
[ 79-39-0 ]
[ 423184-29-6 ]
[ 500367-36-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	In tetrahydrofuran; at 100℃; for 72h;	(A-127) A solution mixture of the above-mentioned compound A-126(6.52g, 28.2mmol) and 2-methylacrylamide(5.28g, 62.1mmol) in tetrahydrofuran(100ml) was stirred for 3 days at 100C. To the solution was added water and extracted with ethyl acetate, washed, dried and evaporated under reduced pressure.. The residue was purified with silica gel column chromatography(chloroform) to give 4-(4-fluorobenzyl)-2-isopropenyloxazole(5.68g, yield:93%). NMR(CDCl3)delta:2.15-2.16(3H, m), 3.86(2H, s), 5.35-5.36(1H, m), 5.91-5.92(1H, m), 6.97-7.03(2H, m), 7.15-7.16(1H, m), 7.22-7.24(2H, m).

Reference： [1]Patent: EP1422218,2004,A1 .Location in patent: Page 124

36
[ 75-86-5 ]
[ 49562-37-0 ]
[ 13027-88-8 ]
[ 79-39-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 85 - 101℃; for 0.666667h;CSTR reactor;Product distribution / selectivity;	A first hydrolysis process (?Prior Art?) of the type disclosed in Kirk-Othmer and US '093 is illustrated by FIG. 2, and comprised two CSTR reactors in series. This system was operated at an H2SO4:ACH molar ratio of 1.48, and at a 2.3:1 ACH addition split, wherein 70% by weight of the total ACH feed was added to the first reaction stage, and 30% by weight of the total ACH feed was added to the second reaction stage. Sulfuric acid at a concentration of 99.5% and ACH at a concentration of 98.5% were utilized as reactants in this system. Specifically, the 1st reaction stage of the hydrolysis system employed in this example comprised a 1st stage CSTR 230, a centrifugal pump 210, a heat exchanger 220, and associated 1st stage circulation piping (203,204,205). CSTR 230 comprised a 5000 gal (19 cubic meters) vessel and a dual-impeller, pitched-blade agitator for high-efficiency mixing of the reactor contents. Sub-surface ACH addition to the 1st stage CSTR 230 was provided via 201 using a first dip-pipe. Similarly, Sub-surface Sulfuric Acid addition to the 1st stage CSTR 230 was provided via 202 using a second dip-pipe. These dip-pipes served to direct the flow of reactants into the turbulent zone near the tip of the agitator blades in order to maximize efficiency of the mixing. PTZ inhibitor in acetone solution (not shown) was also added into CSTR 230 to retard polymer formation. The temperature of the bulk liquid in the bottom of CSTR 230 could be monitored using thermocouple T230. Stream 203 provides hydrolysis mix to Pump 210, which then circulated hydrolysis mix through the 1st stage circulation piping at a continuous rate of about 2.8 million lbs/hr (i.e., 4000 gpm, 15,140 liters/min). Stream 204 conveyed the hydrolysis mix from the discharge of pump 210 to heat exchanger 220, where it was cooled. Heat exchanger 220 was a shell-and-tube type exchanger, with the process flow (hydrolysis mix) passing through the shell side and a nominal 60 C. tempered water flow passing through the tube side. Cooled hydrolysis mix exited the heat exchanger via stream 205 and was returned to CSTR 230. Gases removed from the hydrolysis mix were vented to a process flare header (not shown) for disposal. Degassed hydrolysis mix overflowed from the side of CSTR 230 and was conveyed forward to the 2nd reaction stage via stream 209. The 2nd reaction stage of the hydrolysis system employed in this example comprised a 2nd stage CSTR 260, a centrifugal pump 240, a heat exchanger 250, and associated 2nd stage circulation piping (213,214,215). CSTR 260 comprised a 5000 gal (19 cubic meters) vessel and a dual-impeller, pitched-blade agitator for high-efficiency mixing of the reactor contents. Sub-surface ACH addition to the 2nd stage CSTR 230 was provided via 211 using a first dip-pipe. Optional Sub-surface Sulfuric Acid (212) addition to the 2nd stage CSTR 230 was not used in this example. As with the 1st stage CSTR dip-pipes, these 2nd stage dip-pipes served to direct the flow of reactants into the turbulent zone near the tip of the agitator blades in order to maximize efficiency of the mixing. The temperature of the bulk liquid in the bottom of CSTR 260 could be monitored using thermocouple T260. Stream 213 provided hydrolysis mix to Pump 240, which then circulated hydrolysis mix through the 2nd stage circulation piping at a continuous rate of about 4.2 million lbs/hr (i.e., 6000 gpm, 22,700 liters/min). Stream 214 conveyed the hydrolysis mix from the discharge of pump 240 to heat exchanger 250, where it was cooled. Heat exchanger 250 was a shell-and-tube type exchanger, with the process flow (hydrolysis mix) passing through the shell side and a nominal 65 C. tempered water flow passing through the tube side. Cooled hydrolysis mix exited the heat exchanger via stream 215 and was returned to CSTR 260. Gases removed from the hydrolysis mix were vented to a process flare heater (not shown) for disposal. Degassed hydrolysis mix overflowed from the side of CSTR 260 and was conveyed forward to the cracker reactor (100) via Stream 219. In this example, the bulk temperature of the reaction mixture exiting the 1st reaction stage CSTR (230), as measured by thermocouple T230, was held constant at 85 C.; the bulk temperature of the reaction mixture exiting the 2nd reaction stage CSTR (260), as measured by thermocouple T260, was held constant at 101 C. Under steady state conditions, samples of the final hydrolysis mix were collected from stream 219 using well-insulated sample containers (Thermos brand vacuum bottles). An aliquot (10 g) of the representative Hydrolysis mix was removed and placed in a tared jar containing a stir bar and its weight was recorded. Methanesulfonic acid (99.5% purity, 3 g, from Aldrich Chemical Company) was added as an internal standard via a syringe and the weights were all recorded. The mixture was stirred in a constant temperature water bath at 60 C. for 40 min. An aliquot (0.2 g) of the resulting mixture was removed and ...
	With sulfuric acid;10H-phenothiazine; In acetone; at 79 - 101℃; for 1.83333h;Continuous process;Product distribution / selectivity;	An improved hydrolysis system (?Inventive?), in accordance with the method of the present invention, is illustrated in FIG. 1 and comprised two continuous flow reaction stages. This system was operated under the same conditions used for the CSTR-based hydrolysis system of the preceding Example 1. Specifically, this improved hydrolysis system was operated at an H2SO4:ACH molar ratio of 1.48, and at a 2.3:1 ACH addition split, wherein 70% by weight of the total ACH feed was added to the first reaction stage and 30% by weight of the total ACH feed was added to the second reaction stage. As in the previous example, Sulfuric acid at a concentration of 99.5% and ACH at a concentration of 98.5% were utilized as reactants. The 1st reaction stage of the hydrolysis system employed in this example comprised an ACH mixing apparatus 10, a degassing apparatus 20, a centrifugal pump 30, a heat exchanger 40, and associated 1st stage circulation piping (3,4,5,7,8). Sulfuric Acid (6) was added into the hydrolysis mix in stream 5 through a mixing tee. Stream 5 provided hydrolysis mix to Pump 30, which then circulated hydrolysis mix through the 1st stage circulation piping at a continuous rate of about 2.5 million lbs/hr (i.e., 3500 gpm, 13,250 liters/min). Stream 7 conveyed the hydrolysis mix from the discharge of pump 30 to heat exchanger 40, where it was cooled. Heat exchanger 40 was a shell-and-tube type exchanger, with the process flow (hydrolysis mix) passing through the shell side and a nominal 60 C. tempered water flow passing through the tube side. Cooled hydrolysis mix exited the heat exchanger via stream 8. The temperature of the cooled hydrolysis mix could be monitored using thermocouple T8. The hydrolysis mix then entered the ACH mixing apparatus 10, wherein ACH was added into the hydrolysis mix stream. The ACH mixing apparatus 10 comprised a single static mixing unit consisting of four Koch SMXL mixing elements (available from Koch-Glitsch, Inc. of Wichita, Kans.) installed in series within a 12 diameter piping section. The static mixing unit was approximately 190 inches in length. The ACH mixing apparatus 10 further comprised two sets of ACH injectors: a first set of four injectors (1) located at a distance of about 30 from the inlet end of the mixing apparatus and a second set of four injectors (2) located at a distance of about 45 from the inlet end of the mixing element. Each of the four injectors in a set were evenly-spaced along the circumference of the pipe section-e.g., one injector each positioned at 0, 90, 180, and 270 relative to the pipe section centerline. Each injector comprised a 0.290 internal diameter orifice, flush-mounted to the piping section wall, through which liquid ACH flowed at a velocity of about 36 feet per second (11 meters per second) into the static mixing unit. At this velocity, a jet of ACH was produced having sufficient kinetic energy to traverse from the pipe section wall toward the centerline of the static mixing unit, thereby ensuring rapid and efficient mixing. For the operating rate of this specific example, six of the eight injectors were utilized: all four of the first set of injectors and two of the second set of injectors. Of the injectors in operation, all were operated at the same ACH flow rate. As a result of the exothermic ACH hydrolysis reaction, the hydrolysis mix warmed within the ACH mixing apparatus. The warm hydrolysis mix exited the ACH mixing apparatus via stream 3 and entered the degassing apparatus 20. PTZ inhibitor in acetone solution (9) was added into the hydrolysis mix stream 3 to retard polymer formation. Degassing apparatus 20 comprised an unagitated 5,600 gallon (21 cubic meters) degassing vessel in which was installed a ?Porta-Test Revolution? model centrifugal gas,liquid separator (designed and manufactured by NATCO Group, Inc. of Houston, Tex.). Gases removed from the hydrolysis mix were vented to a process flare header (not shown) for disposal; the degassed hydrolysis mix collected as a bulk liquid in the bottom of the degassing vessel. The temperature of the bulk liquid in the bottom of the degassing vessel could be monitored using thermocouple T20. Degassed hydrolysis mix was withdrawn from the bottom of the degassing vessel and was divided into two streams: stream 49 conveyed a first portion of the hydrolysis mix forward to the 2nd reaction stage, while stream 5 returned a second portion of the hydrolysis mix to centrifugal pump 30 to maintain the 1st stage circulation. The 2nd reaction stage of the inventive hydrolysis system employed in this example comprised an ACH mixing apparatus 50, a degassing apparatus 60, a centrifugal pump 70, a heat exchanger 80, and associated 2nd stage circulation piping (13,14,15,17,18). Hydrolysis mix from stream 49 entered the 2nd stage and was combined with the hydrolysis mix in stream 15. In this specific example, optional sulfuric acid (16) was not added. Stream 15 provided hydrolysis mix to Pump 70, which th...

Reference： [1]Patent: US2006/111586,2006,A1 .Location in patent: Page/Page column 5-6; 8
[2]Patent: US2006/111586,2006,A1 .Location in patent: Page/Page column 6-8

37
[ 541-41-3 ]
[ 79-39-0 ]
[ 53580-39-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In 1,4-dioxane; water;	EXAMPLE 1 In 41 g of dioxane, 2.5 g of methacrylamide and 1.18 g of NaOH were dissolved and the solution was stirred for 1.0 hour at the temperature of 25 to 27 C. Then, 4.0 g of ethyl chloroformate was dissolved in 10 g of dioxane and the solution was added to the reaction mixture at once. After stirring the solution for 15 minutes, water was added thereto and the solution was neutralized by adding conc. hydrochloric acid and filtered. The filtrate was extracted with chloroform and the extract was evaporated in vacuo. The crude product was subjected to column chromatography for purification, thereby obtaining 0.841 g of ethyl N-methacryloylcarbamate. Melting point (mp.) of the compound was 73-74 C.
	In 1,4-dioxane; water;	EXAMPLE 3 In 200 g of dioxane, 4.26 g of methacrylamide and 6.37 g of potassium t-butoxide were dissolved and the solution was stirred for 60 minutes at 60 C. Then, 5.43 g of ethyl chloroformate was dissolved in 50 g of dioxane and the solution was added dropwise to the reaction mixture in 2 hours. After removing tetrahydrofurane in vacuo, 1000 g of water was added to the residue and the solution was extracted with 500 ml of ethyl acetate. The extract was evaporated in vacuo. The crude product was subjected to column chromatography, thereby obtaining 1.0 g of ethyl N-methacryloylcarbamate. Melting point of the product was 73-74 C.

Reference： [1]Patent: US5187306,1993,A
[2]Patent: US5187306,1993,A

38
ethyl chloroformate acid [ No CAS ]
[ 79-39-0 ]
[ 53580-39-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In 1,4-dioxane;	EXAMPLE 2 In 52 g of dioxane, 12.5 g of methacrylamide and 1.0 g of sodium ethoxide (NaOEt) were dissolved and the solution was stirred for 20 minutes at the temperature of 27 C. Then, 4.0 g of ethyl chloroformate acid was dissolved in 2 g of dioxane and the solution was added in two portions into the above reaction solution. After leaving it for one day, the solution was neutralized with conc. hydrochloric acid and was extracted with chloroform. The extract was evaporated in vacuo. The crude product was subjected to column chromatography, thereby obtaining 0.44 g of ethyl N-methacryloylcarbamate. Melting point of the compound was 73-74 C.

Reference： [1]Patent: US5187306,1993,A

39
[ 79-39-0 ]
[ 80-62-6 ]

Yield	Reaction Conditions	Operation in experiment
39.5%	1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol;	EXAMPLE 17 The reaction was conducted by the same procedure in the same autoclave as Example 1, except that 70 mmol of methacrylamide and 560 mmol of methanol were used with 3.0 mmol of DBU as the catalyst. The conversion of methacrylamide was 39.5%, the yield of methyl methacrylate was 34.6%, and the selectivity was 87.6%. The yield of formamide by this reaction was 35.1% with the selectivity of 88.9%.

Reference： [1]Patent: US4613684,1986,A

40
[ 79-37-8 ]
[ 25088-52-2 ]
[ 79-39-0 ]
[ 95-50-1 ]
[ 4474-60-6 ]

Yield	Reaction Conditions	Operation in experiment
88.4%	In hexane;	EXAMPLE 19 Oxalyl chloride (139.6 g; 1.1 mol) and o-dichlorobenzene (400 g; dielectric constant, 9.88) were mixed together and cooled to a temperature of 0 to 10 C. <strong>[79-39-0]<strong>[79-39-0]Methacrylamid</strong>e</strong> (85.1 g; 1.0 mol) was portionwise added thereto in 40 minutes, followed by stirring at 35 to 40 C. for 2 hours. A small amount of seed crystals of 2-isopropenyl-oxazoline-4,5-dione hydrochloride was added thereto, and the resultant mixture was allowed to stand whereby 2-iso-propenyloxazoline-4,5-dione hydrochloride was crystallized out. To the above mixture comprising crystals of 2-isopropenyloxazoline-4,5-dione hydrochloride, hexane (600 g; dielectric constant, 1.88) was added so that the dielectric constant of the solvent mixture was made to 3.45. Stirring was continued at a temperature of 70 to 75 C. for 1.5 hours. Distillation of the reaction mixture gave methacryloyl isocyanate (55.9 g). Yield, 88.4%.
88.4%	In hexane;	Example 18 Oxalyl chloride (139.6 g; 1.1 mol) and o-dichlorobenzene (400 g; dielectric constant, 9.88] were mixed together and cooled to a temperature of 0 to 10C. <strong>[79-39-0]<strong>[79-39-0]Methacrylamid</strong>e</strong> (85.1 g; 1.0 mol) was portionwise added thereto in 40 minutes, followed by stirring at 35 to 40C for 2 hours. A small amount of seed crystals of 2-isopropenyloxazoline-4,5-dione hydrochloride was added thereto, and the resultant mixture was allowed to stand whereby 2-isopropenyloxazoline-4,5-dione hydrochloride was crystallized out. To the above mixture comprising crystals of 2-isopropenyloxazoline-4,5-dione hydrochloride, hexane (600 g; dielectric constant, 1.88) was added so that the dielectric constant of the solvent mixture was made to 3.45. Stirring was continued at a temperature of 70 to 75C for 1.5 hours. Distillation of the reaction mixture gave methacryloyl isocyanate (55.9 g). Yield, 88.4 %.

Reference： [1]Patent: US4769485,1988,A
[2]Patent: EP202840,1991,B1

41
[ 79-39-0 ]
[ 17858-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	With methyloxirane; In acetic acid methyl ester;	EXAMPLE 5 85g of methacrylic amide are suspended in 120g of methyl acetate in the apparatus described in Example 1 and 210g of hydrogen bromide are introduced into this suspension at a temperature below 40C. Subsequently and at a temperature below 50C, 91g of propylene oxide are added in doses. From the reaction mixture, 45g of methyl acetate are then distilled off in the rotation evaporator. Subsequently the mixture is cooled in an ice bath, whereby the beta-bromoisobutyric amide formed crystallizes out. It is filtered off, washed with a little methyl acetate and dried. The yield amounts to 117g corresponding to 70.5% of the theory. The melting point lies between 95 and 102C.

Reference： [1]Patent: US3963674,1976,A

42
[ 79-41-4 ]
[ 79-39-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	With diphenyl-phosphinic acid; triethylamine; In THF-n-hexane; chloroform; N,N-dimethyl-formamide;	EXAMPLE 7 Synthesis of biotinamine methacrylamide (Compound G) In 5 ml of DMF (solvent) were dissolved 100 mg (0.38 mmol) of biotinamine hydrochloride and 38 mul (0.43 mmol) of methacrylic acid. The resulting solution was kept at 0C, followed by stirring. To the reaction mixture was added dropwise 130 mul (0.5 mmol) of DPPA and the mixture was kept at 0C. A solution obtained by dissolving 156 mul (1.1 mmol) of triethylamine in 1 ml of DMF was added dropwise and the mixture was stirred for 2 to 4 hours at 0C. The reaction mixture was allowed to stand at room temperature and the reaction was continued overnight. After completion of the reaction, DMF was distilled off under reduced pressure. The residue was dissolved in chloroform. The chloroform layer was washed with 1N hydrochloric acid, NaHCO3and water. The solvent was then removed. The residue was dissolved in a THF-n-hexane solvent mixture, whereby 40 mg of biotinamine methacrylamide (Compound G) was obtained as a precipitate (yield: 35%).

Reference： [1]Patent: EP1201667,2002,A1

43
[ 79-39-0 ]
[ 44810-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In hydrogenchloride;	EXAMPLE 1-1 Synthesis of N-acetyl (meth)acrylamide (Scheme a) In an atmosphere of nitrogen gas, 30.5 g of acrylamide, 80 g of N,N-dimethylacetamide dimethylacetal and 400 ml of THF were charged in a flask, and then stirred at a temperature of 65C for 3 hours. The reaction solution thus obtained was concentrated under reduced pressure. The residue was subjected to simple distillation under a pressure of 1 mmHg to obtain 45 g of an acroylimide. The acroylimide thus obtained was dissolved in 100 ml of a 2 N hydrochloric acid, and then charged into a flask. To the solution was then added 20 ml of acetic acid. The mixture was then stirred at room temperature for 4 hours. The reaction solution was then extracted with ethyl acetate. The resulting organic phase was then concentrated under reduced pressure. The residue was then subjected to column chromatography with ethyl acetate as a solvent. The resulting fraction was then concentrated under reduced pressure. The residue was then recrystallized from ethyl acetate as a solvent to obtain 30 g of a white crystal. The above described synthesis procedure was followed except that 30.5 g of methacrylamide was used as a starting material. As a result, 32 g of the desired compound was obtained. NMR analysis gave a strong indication that the product is the desired compound.

Reference： [1]Patent: EP922715,1999,A2

44
[ 79-37-8 ]
2-isopropenyloxazoline-4-5-dione hydrochloride [ No CAS ]
[ 79-39-0 ]
[ 95-50-1 ]
[ 25088-52-2 ]

Yield	Reaction Conditions	Operation in experiment
98.6%	In hexane;	Example 24 Oxalyl chloride (139.6 g; 1.1 mol) and o-dichlorobenzene (400 g; dielectric constant, 9.88) were mixed together and cooled to a temperature of 0 to 10C. <strong>[79-39-0]<strong>[79-39-0]Methacrylamid</strong>e</strong> (85.1 g; 1.0 mol) was portionwise added thereto in 40 minutes. A small amount of seed crystals of 2-isopropenyloxazoline-4-5-dione hydrochloride was added thereto, and the resultant mixture was allowed to stand whereby 2-isopropenyloxazoline-4,5-dione hydrochloride was crystallized out. Hexane (600 g; dielectric constant, 1.88) was added thereto. Precipitated crystals were collected by filtration to obtain 2-isopropenyloxazoline-4,5-dione hydrochloride in a yield of 98.6 %.

Reference： [1]Patent: EP202840,1991,B1

45
propyl 4-O-(2-O-sulfonato-β-D-glucopyranosiduronate)-2,6-di-O-sulfonato-β-D-glucopyranoside tetrasodium salt [ No CAS ]
[ 97-90-5 ]
[ 79-39-0 ]
2-aminoethylmethacrylate hydrochloride [ No CAS ]
propyl 4-O-(2-O-sulfonato-β-D-glucopyranosiduronate)-2,6-di-O-sulfonato-β-D-glucopyranoside tetrasodium salt-imprinted methylacrylamide, 2-aminoethyl methacrylate, ethyl glycol dimethylacrylate copolymer [ No CAS ]

Reference： [1]Carbohydrate Research,2008,vol. 343,p. 587 - 595

46
[ 97-90-5 ]
[ 79-39-0 ]
2-aminoethylmethacrylate hydrochloride [ No CAS ]
methylacrylamide, 2-aminoethyl methacrylate, ethyl glycol dimethylacrylate copolymer [ No CAS ]

Reference： [1]Carbohydrate Research,2008,vol. 343,p. 587 - 595

47
[ 1295-35-8 ]
[ 79-39-0 ]
[ 96055-24-2 ]
(1,3-diphenylphosphinoethane)NiCH₂CH(Me)CONH [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7448

48
[ 1295-35-8 ]
[ 132610-59-4 ]
[ 79-39-0 ]
NiCH₂CH(CH₃)CONH(P(C₆⁽²⁾H₁₁)3) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7448

49
[ 1295-35-8 ]
[ 79-39-0 ]
[ 554-70-1 ]
[ 75597-53-4 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7448

50
[ 1295-35-8 ]
[ 79-39-0 ]
[ 72251-33-3 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7448

51
[ 1295-35-8 ]
[ 79-39-0 ]
[ 7650-89-7 ]
Ni*0.5CH₂C(CH₃)CONH₂*2P(C₆H₅CH₂)3 = Ni(CH₂C(CH₃)CONH₂)0.5(P(C₆H₅CH₂)3)2 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7448

52
[ 79-39-0 ]
polypropylene [ No CAS ]
polypropylene-graft-polymethacrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,5-dimethyl-2,5-bis(tert-butylperoxy)-3-hexyne; at 185℃; for 0.166667h;	A mixture containing 40 grams PP, 1.02 grams MAM (300 mpm) and 0.11 grams DTBHY (10 mpm) were dry mixed together for 5 min and introduced in the preheated chamber for at 50 rpm for 5 min at 185 0C. Similarly purification was done as discussed above.

Reference： [1]Patent: WO2008/48749,2008,A2 .Location in patent: Page/Page column 42

53
[ 79-41-4 ]
[ 3775-90-4 ]
[ 97-63-2 ]
[ 79-39-0 ]
[ 79-10-7 ]
poly(acrylic acid-co-N-tert-butylaminoethyl methacrylate-co-ethyl methacrylate-co-methacrylamide-co-methacrylic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of 500 g of a 30% strength by weight ethanol/water [2.1:1] solution of a polymer of the composition EMA/MAM/MAS/AS/NtBAEMA 65/7/22/3/3 In a stirred apparatus with reflux condenser, internal thermometer and four separate feed devices, 16.6 g of feed 1, 0.85 of feed 2, 27 g of water and 40 g of ethanol were initially introduced and the mixture was heated to about 65 C. with stirring. After the onset of polymerization, evident from a slight increase in viscosity, the remainder of feed 1 was added over the course of three hours and the remainder of feed 2 was added over the course of 4 hours at 67 C. The reaction solution was after-stirred for about a further two hours at 70 C. Feed 3 was metered in at about 70 C. over 30 minutes. The polymer mixture was after-polymerized for about a further two hours at 80 C. The polymer solution was neutralized with AMP in feed 4 over 10 minutes. This gave 500 g of an approximately 30% strength by weight of aqueous-ethanolic polymer solution.

Reference： [1]Patent: US2008/286221,2008,A1 .Location in patent: Page/Page column 21-22

54
[ 79-39-0 ]
[ 536-74-3 ]
[ 1095320-54-9 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 8492 - 8495
[2]Synthesis,2009,p. 2283 - 2288

55
[ 106-92-3 ]
[ 2359-15-1 ]
[ 106-91-2 ]
[ 79-39-0 ]
poly(allylglycidyl ether-co-glycidyl methacrylate-co-methacrylamide-co-methylene-bismethacrylamide-co-2-trimethylammonium-ethyl methacrylate chloride) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4,4'-dicyano-4,4'-azo-di-valeric acid; 2-methyl-butyl acrylate; [2-(methacryloyloxy)ethyl]trimethylammonium chloride; In methanol; cyclohexane; water; at 50 - 70℃; for 6h;	An organic solvent and 3 g of a copolymer composed of 95 parts by n-butyl methacrylate and of 5 parts of 2-trimethylammoniumethyl methacrylate chloride as protective colloid are used as initial charge in a 2 l stirred flask with thermometer, reflux condenser, nitrogen inlet tube. A monomer phase composed of diluent, and also 100 g of the monomer mixture stated in Table 1 and also 2 g of 4,4'-azobis-4-cyanovaleric acid (as polymerization initiator) are dispersed at 50 C., with stirring and nitrogen flushing, in the organic phase, and the mixture is then heated to boiling at from 65 to 70 C. The mixture is stirred for about 6 hours and then cooled to room temperature. The resultant polymer beads are isolated by suction filtration, washed, and dried in a fluidized-bed dryer. The binding capacity for penicillin amidase [U/g, moist] is then determined at various salt concentrations, and the binding yield and the swelling index [ml, moist/ml, dry] are determined. The results are collated in Table 2.

Reference： [1]Patent: US2007/259968,2007,A1 .Location in patent: Page/Page column 5-6

56
[ 79-39-0 ]
[ 501-65-5 ]
[ 1256971-43-3 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5665 - 5668
[2]Organic Letters,2010,vol. 12,p. 5462 - 5465

57
[ 393-09-9 ]
[ 79-39-0 ]
[ 90357-52-1 ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1049 - 1056

58
[ 110-20-3 ]
[ 79-39-0 ]
2-imino-5,5-dimethyl-Δ³-1,3,4-oxadiazoline [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2012,vol. 24,p. 288 - 290

59
[ 3900-89-8 ]
[ 79-39-0 ]
[ 31883-79-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2128 - 2131

60
[ 2058-72-2 ]
[ 79-39-0 ]
[ 609-36-9 ]
5-bromo-1,2'-dimethyl-2-oxo-1,1',2,2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizine]-2'-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In methanol; water; for 2h;Reflux;Mechanism;	General procedure: A mixture of isatin(1.0 mmol), alpha-amino acid (1.0 mmol) and acrylamide (1.0 mmol) in 4.0 mL aqueous methanol (1:3) was heated in an oil bath to reflux temperature for 40 min to 7 hours. The resulting precipitates were collected by filtration and washed with cold methanol to give the analyticallypure products 4.

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 117 - 126

61
[ 2094-72-6 ]
[ 79-39-0 ]
[ 1430224-90-0 ]

Yield	Reaction Conditions	Operation in experiment
194.4 g		Monomer Synthesis Example Examples 1 to 9 Example 1 90.0 g of methacrylamide was dissolved in 1,350 g of tetrahydrofuran (THF), and 944 mL of a 1.12 mol/L lithium diisopropylamide (LiDA) solution was dropwise added thereto at 5 C., followed by stirring for 10 minutes. Subsequently, 900 g of THF having 231.1 g of 1-adamantanecarbonyl chloride dissolved therein was added thereto, followed by stirring at 5 C. for 18 hours. After completion of the reaction, THF and t-butylmethylether (TBME) were added thereto, followed by washing with a 1 wt % aqueous hydrochloric acid solution and pure water, and concentration under reduced pressure. n-hexane was added to the obtained solution, and crystallization was conducted at 5 C., followed by filtration. The obtained solid was dried under reduced pressure, thereby obtaining 194.4 g of 1-adamantanecarboxylic acid methacrylamide (compound (51)). With respect to the obtained compound (51), the results of the proton nuclear magnetic resonance spectrum (1H-NMR) are shown below. [0790] 1H-NMR (DMSO-d6, internal standard: tetramethylsilane): delta=9.85 ppm (br s, 1H), 5.57 ppm (s, 1H), 5.51 ppm (s, 1H), 1.98 ppm (m, 3H), 1.86 ppm (m, 9H), 1.61 ppm (m, 6H)
194.4 g		90.0 g of methacrylamide was dissolved in 1350 g of tetrahydrofuran (THF), thereto, at 5 C 944 mL of lithium diisopropylamide (LiDA) 1.12 mol/L was dropped and stirred for 10 minutes. Subsequently, 231.1 g of 1-adamantanecarbonyl chloride dissolved in 900 g of THF was added thereto, and the mixture was stirred at 5 C for 18 hours. After completion of the reaction, THF and t-butyl methyl ether (TBME) were added, washed with a 1% by mass aqueous hydrochloric acid solution and pure water, and then concentrated under reduced pressure. To the resulting solution was added n-hexane, After crystallization at 5 C., filtration was carried out, and the obtained solid was dried under reduced pressure 194.4 g of 1-adamantanecarboxylic acid methacrylamide (compound (51)) was obtained.
194.4 g		90.0 g of methacrylamide,Was dissolved in 1350 g of tetrahydrofuran (THF)there,944 mL of lithium diisopropylamide (LiDA) 1.12 mol / L solution was dropped at 5 C., and the mixture was stirred for 10 minutes.Then,there,231.1 g of 1-adamantanecarbonyl chloride dissolved in 900 g of THF was added,Followed by stirring at 5 C. for 18 hours.After completion of the reaction,THF and t-butyl methyl ether (TBME)After washing with 1 mass% hydrochloric acid aqueous solution and pure water, the mixture was concentrated under reduced pressure.To the obtained solution was added n-hexane,After crystallization at 5 C., filtration was carried out,The obtained solid was dried under reduced pressure to obtain 194.4 g of 1-adamantanecarboxylic acid methacrylamide (compound (51)).

Reference： [1]Patent: US2014/221673,2014,A1 .Location in patent: Paragraph 0788-0790
[2]Patent: JP2016/84350,2016,A .Location in patent: Paragraph 0292; 0293
[3]Patent: JP2017/81990,2017,A .Location in patent: Paragraph 0292-0293

62
[ 1864-94-4 ]
[ 79-39-0 ]
[ 5615-90-7 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 5960 - 5963

63
[ 79-39-0 ]
[ 106-45-6 ]
2-hydroxy-2-methyl-3-(p-tolylthio)propanamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1180 - 1183

64
[ 288-13-1 ]
[ 79-39-0 ]
C₇H₁₁N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-benzyl-trimethylammonium hydroxide; In methanol; for 2.75h;Inert atmosphere; Heating;	In a 150 mL three-neck flask, a mixture of pyrazole (5.00 g,73.5 mmol), 2-methylacrylamide (6.25 g, 73.5 mmol) and 2 mL ofTriton B was heated for 2.75 h in a boiling water bath under Argas. The mixture solidified upon cooling. The crude product wasslurried with 25 mL of a 4:1 methylene chloride/diethyl ethermixture, filtered and washed with an additional 35 mL of themethylene chloride/diethyl ether mixture. After drying under vacuum10.72 g (70.0 mmol, 95%) of 1 was obtained. Single crystals suitable for X-ray diffraction were obtained by recrystallizationfrom dichloromethane. mp = 128.6-128.9 C. Anal. Calc. forC7H11N3O (Mr = 153.18): C, 54.88; H, 7.24; N, 27.43. Found: C,54.66; H, 7.02; N, 27.0%. IR (KBr, cm1): 3357 (vs), 3178 (vs),3113 (m), 2986 (m), 2968 (m), 2941 (w), 1668 (vs), 1630 (vs), 1511 (mw), 1470 (m), 1442 (m), 1397 (ms), 1315 (m), 1280(ms), 1270 (m), 1188 (m), 1141 (mw), 1084 (m), 1049 (mw),970 (mw), 944 (mw), 917 (m), 777 (ms), 758 (m), 653 (ms), 641(m), 522 (m). 1H NMR (300 MHz, CDCl3): 7.53 (1Hc, dd, Jbc = 1.9 -Hz, Jac = 0.7 Hz), 7.42 (1Ha dd, Jab = 2.3 H, Jac = 0.7 Hz), 6.23 (1Hb dd, Jbc = 1.9 Hz, Jab = 2.3 Hz), 5.84 (NH s br), 5.46 (NH, s br), 4.36(1Hd, Jdd0 = 13.7 Hz, Jde = 8.9 Hz) and 4.18 (1Hd0 , Jd0e = 5.4Jdd0 = 13.7 Hz), 3.05 (1He, dqd, Jde = 5.4 and 8.9 Hz, Jeg = 7.0 Hz),1.21 (3Hg, Jeg = 7.0 Hz) ppm. The spectrum is not first order andwas simulated using Spinworks 4.0.5.0. 13C{1H} NMR (75.5 MHz,CDCl3): 175.8 (Cf), 139.5 (Ca), 130.3 (Cc), 105.0 (Cb), 54.5 (Cd),41.3 (Ce), 15.3 (Cg). The assignment of Ca, Cb, and Cc is based onanalogy to N-methylpyrazole [14,26].

Reference： [1]Polyhedron,2015,vol. 88,p. 178 - 187

65
[ 555-16-8 ]
[ 79-39-0 ]
N,N'-[(4-nitrophenyl)methylene]bis(2-methylacrylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With camphor-10-sulfonic acid; In toluene; at 20℃;Reflux;	General procedure: The appropriate amide (2 mmol) was refluxed in dry toluene (25 mL) until it dissolved completely. To this solution was added dropwise a mixture of the appropriate aldehyde (1 mmol) and CSA (0.05 mmol) in toluene (3-5 mL) at r.t., and the resulting mixture was refluxed for 2-5 h then cooled. The precipitate that formed was collected by filtration with suction. The solid product was washed successively with benzene (2-3 mL) and Et2O (2 × 5 mL) to give an analytically pure product.

Reference： [1]Synthesis,2015,vol. 47,p. 2976 - 2984

66
4-methylphenylene-1,3-bisdiazonium tetrafluoroborate [ No CAS ]
[ 333-20-0 ]
[ 79-39-0 ]
3-(4-methyl-3-thiocyanatophenyl)-2-methyl-2-thiocyanatopropionamide [ No CAS ]