[ CAS No. 372198-49-7 ]

Name: 5-Cyano-2-methylbenzenesulfonyl chloride
Brand: Ambeed
SKU: A628797
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Quality Control of [ 372198-49-7 ]

COA GC NMR CNMR HPLC/UPLC LC-MS

Related Doc. of [ 372198-49-7 ]

SDS

Product Details of [ 372198-49-7 ]

CAS No. :	372198-49-7	MDL No. :	MFCD09741164
Formula :	C₈H₆ClNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	215.66	Pubchem ID :	16794335
Synonyms :

Computed Properties of [ 372198-49-7 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 372198-49-7 ]

Signal Word:	Danger	Class	8
Precautionary Statements:	P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 372198-49-7 ]

Downstream synthetic route of [ 372198-49-7 ]

[ 372198-49-7 ] Synthesis Path-Downstream 1~9

1
[ 372198-49-7 ]
C₁₄H₂₂N₂O [ No CAS ]
C₂₂H₂₇N₃O₃S [ No CAS ]

Reference： [1]MedChemComm,2017,vol. 8,p. 942 - 951

2
[ 372198-49-7 ]
(R)-1-([1,1′-biphenyl]-4-ylmethyl)pyrrolidin-3-amine hydrochloride [ No CAS ]
C₂₅H₂₅N₃O₂S [ No CAS ]

Reference： [1]MedChemComm,2017,vol. 8,p. 942 - 951

3
[ 372198-49-7 ]
(R)-1-(4-cyclopropoxybenzyl)pyrrolidin-3-amine hydrochloride [ No CAS ]
C₂₂H₂₅N₃O₃S [ No CAS ]

Reference： [1]MedChemComm,2017,vol. 8,p. 942 - 951

4
[ 372198-49-7 ]
C₈H₈ClN₅ [ No CAS ]
(E)-N'-((5-chloropyrazolo[1,5-a]pyrimidin-3-yl)methylene)-5-cyano-N,2-dimethylbenzenesulfonohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
116 mg	In methanol; at 20℃;	General procedure: These were made using one of either method A or method B. 4.1.2.1. General method A. To a solution of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (8) (1 equiv) in anhydrous MeOH (0.1 M) was added NaHCO3 (5 equiv) followed by methylhydrazine sulfate (1.2 equiv). After stirring for 2 h at RT the sulfonyl chloride was added (1.3 equiv) and the reaction was stirred for a further hour. The MeOH was removed in vacuo and the orange residue was partitioned between CH2Cl2 and water. The aqueous phase was washed with CH2Cl2, the organic phases were combined, dried (Whatman PS1 filter paper) and the solvent was removed in vacuo. The crude material was adsorbed onto silica and purified by automated flash chromatography on silica gel (generally 0-50% EtOAc-cyclohexane) to yield the desired product. 4.1.2.2. General method B. Using the same procedure as Method A however NaHCO3 was replaced with 2,6-lutidine. Following stirring for up to 16 h the precipitate was isolated by filtration, dried (Whatman PS1 filter paper) in vacuo and purified as for Method A.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6280 - 6296

5
[ 372198-49-7 ]
C₈H₉ClN₄ [ No CAS ]
N-(2-(5-chloropyrazolo[1,5-a]pyrimidin-3-yl)ethyl)-2-methyl-5-cyanobenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27.7 mg	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;	A solution of 5-chloro-3-(2-nitroethyl)pyrazolo[1,5-a]pyrimidine (15) (45 mg, 0.199 mmol) in MeOH (10 mL) and treated witha spatula of RaNi surrey under hydrogen at RT for 1 h. The reaction mixture was filtered through a pad of Celite and the solvent was removed in vacuo. The resulting material was dissolved in CH2Cl2 (2 mL) and cooled to 0 C. To this was added NEt3 (83 lL,0.597 mmol) followed by <strong>[372198-49-7]2-methyl-5-cyanobenzenesulfonyl chloride</strong> (47 mg, 0.218 mmol). The reaction was allowed to warm slowly to RT and was stirred for 16 h. The reaction was diluted with CH2Cl2 (10 mL) and washed with sat. NaHCO3 (10 mL) and water (2*10 mL) dried (Whatman PS1 filter paper) and solvent was removed in vacuo. After chromatography (40-100% EtOAc-cyclohexane)this gave N-(2-(5-chloropyrazolo[1,5-a]pyrimidin-3-yl)ethyl)-2-methyl-5-cyanobenzenesulfonamide (17b) as a yellow solid (27.7 mg, 37%). 1H NMR deltaH (CDCl3, 300 MHz), 8.54 (d, J 7.3,1H), 8.24 (d, J 1.5, 1H), 7.96 (s, 1H), 7.70 (dd, J 7.9, 1.8, 1H), 7.39(d, J 7.9, 1H), 6.81 (d, J 7.2, 1H), 5.64 (m, 1H), 3.41 (m, 2H), 2.98 (t, J 6.2, 2H), 2.67 (s, 3H); LC-MS tR 5.88 min; LC254 99.0%; m/z390.1/392.2 [M+H].

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6280 - 6296

6
[ 372198-49-7 ]
tert-butyl 6-(4-aminophenyl)-3-[bis(tert-butoxycarbonyl)amino]indazole-1-carboxylate [ No CAS ]
C₃₆H₄₁N₅O₈S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78

7
[ 356092-74-5 ]
[ 372198-49-7 ]
5-cyano-N-cyclopentyl-N-(2,4-dimethoxybenzyl)-2-methylbenzenesulfonamide [ No CAS ]

Reference： [1]MedChemComm,2014,vol. 5,p. 1834 - 1842

8
[ 1101120-05-1 ]
[ 372198-49-7 ]
[ 302-15-8 ]
[ 1101118-28-8 ]

Yield	Reaction Conditions	Operation in experiment
48%		General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 58 - 68

9
[ 60710-80-7 ]
[ 372198-49-7 ]

Yield	Reaction Conditions	Operation in experiment
25%		3-Amino-4-methylbenzonitrile (407 mg, 3.09 mmol) was suspended in concentrated HCl (3 mL) at 0 C. A solution of NaNO2 (320 mg, 4.64 mmol) in water (1 mL) was added dropwise over 5 min, and the solution stirred for 45 min. Meanwhile, AcOH (3 mL) was saturated with SO2, then CuCl2·2H2O (158 mg, 0.93 mmol) was added and SO2 bubbled through for a further 5 min. The AcOH mixture was cooled to 5 C, then the diazonium solution added over 5 min. The resulting mixture was stirred for a further 1.5 h, then the precipitate filtered off, washed with a little water and dried to leave <strong>[372198-49-7]5-cyano-2-methylbenzenesulfonyl chloride</strong> as a yellow solid (167 mg, 25%). 1H NMR delta (400 MHz, CDCl3) 8.36 (d, J = 1.7 Hz, 1H), 7.87 (dd, J = 7.9, 1.7 Hz, 1H), 7.58 (d, J = 7.9 Hz, 1H), 2.88 (s, 3H). LC-MS (APCI-) 196 (M-Cl+O, 100%). Reaction of 2 (30 mg, 0.18 mmol) and the above sulfonyl chloride (45 mg, 0.21 mmol) using NaHCO3, after chromatography (eluting with CH2Cl2:MeOH 99.75:0.25) gave 6j as a yellow solid (32 mg, 48%).
25%		Step 21.1 : 3-Amino-4-methylbe?zonitrile (52: X = Me1 Y = CN) (407 mg, 3.09 mmol) was suspended in concentrated HCI (3 mL) at 0 0C. A solution of NaNO2 (320 mg, 4.64 mmol) in water (1 mL) was added dropwise over 5 mins, and the solution stirred for 45 mins. Meanwhile, AcOH (3 mL) was saturated with SO2, then CuCI2.2H2O (158 mg, 0.93 mmol) was added and SO2 bubbled through for a further 5 mins. The AcOH mixture was cooled to 5 0C, then the diazonium solution added over 5 mins. The resulting mixture was stirred for a further 1.5h, then the precipitate filtered off, washed with a little water and dried to leave <strong>[372198-49-7]5-cyano-2-methylbenzenesulfonyl chloride</strong> (53: X = Me, Y = CN) as a yellow solid (167 mg, 25%). 1H NMR delta (400 MHz, CDCI3) 8.36 (d, J 1.7 Hz, 1 H), 7.87 (dd, J 7.9, 1.7 Hz, 1 H), 7.58 (d, J 7.9 Hz, 1 H), 2.88 (s, 3H). LCMS (APCI ) 196 (M-CI+O, 100%).
		A solution of 3-amino-4-methyl-benzonitrile (454mg) in cone. HCl (3.5mL) and AcOH (4mL) was cooled to -10C. To this was added a solution OfNaNO2 (284mg) in water (2.1ml) dropwise. After stirring for 15 minutes the mixture was added to a cooled (5C) solution of CuCl (85mg) in AcOH (7mL) that had previously been saturated with SO2 gas. The reaction mixture was warmed to room temperature, SO2 was removed in vacuo and then water was added to yield the title compound as a white solid which was collected by filtration. (520mg).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 58 - 68
[2]Patent: WO2009/8748,2009,A1.Location in patent: Page/Page column 73
[3]Patent: WO2009/93049,2009,A1.Location in patent: Page/Page column 37

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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
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H301	Toxic if swallowed
H302	Harmful if swallowed
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 372198-49-7 ]

Quality Control of [ 372198-49-7 ]

Related Doc. of [ 372198-49-7 ]

Product Details of [ 372198-49-7 ]

Computed Properties of [ 372198-49-7 ]

Safety of [ 372198-49-7 ]

Application In Synthesis of [ 372198-49-7 ]

[ 372198-49-7 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 372198-49-7 ]

Nitriles

Sulfonyl Chlorides

Aryls

Precautionary Statements-General

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