[ CAS No. 80-65-9 ] {[proInfo.proName]}

Name: 80-65-9|3-Aminooxazolidin-2-one|95%
Brand: Ambeed
SKU: A179065
Rating: 95 (30 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 80-65-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 80-65-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 80-65-9 ]

SDS Specification

Alternatived Products of [ 80-65-9 ]

Product Details of [ 80-65-9 ]

CAS No. :	80-65-9	MDL No. :	MFCD00020871
Formula :	C₃H₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KYCJNIUHWNJNCT-UHFFFAOYSA-N
M.W :	102.09	Pubchem ID :	65725
Synonyms :	AOZ

Calculated chemistry of [ 80-65-9 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	25.61
TPSA :	55.56 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) :	-7.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.88
Log Po/w (XLOGP3) :	-0.85
Log Po/w (WLOGP) :	-1.07
Log Po/w (MLOGP) :	-0.87
Log Po/w (SILICOS-IT) :	-0.6
Consensus Log Po/w :	-0.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	0.06
Solubility :	118.0 mg/ml ; 1.15 mol/l
Class :	Highly soluble
Log S (Ali) :	0.16
Solubility :	149.0 mg/ml ; 1.46 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.76
Solubility :	586.0 mg/ml ; 5.74 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 80-65-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 80-65-9 ]

* 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 [ 80-65-9 ]
Downstream synthetic route of [ 80-65-9 ]

[ 80-65-9 ] Synthesis Path-Upstream 1~7

1
[ 109-84-2 ]
[ 105-58-8 ]
[ 80-65-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	for 4 h; Reflux	15.2g (0.2mol) 2-hydrazinoethanol (Intermediate 1), 31.0g (0.2mol) diethyl carbonate, and 3.0g (57mmol) sodium methoxide were added to a 100ml three-necked flask, and were refluxed for 4 hours, and after cooling, solids were precipitated, filtrated under vacuum, and dried. The solvent in the mother solution was removed by distillation. After column chromatography (eluent: methanol/dichloromethane (at a ratio of 1:20 by volume)), the obtained white solid and the dried solid were recrystallized in ethanol, to get 15.3g product (Intermediate 2), with a yield of 75percent. ¹H-NMR(400MHz,D2O)δppm:4.33(2H,t,J=8.0Hz,J=8.0Hz),3.94(2H,s),3.70(2H,t,J= 4.0Hz,J=4.0Hz);EI-MS(m/z):103.1[M+H]+; m.p. 64-66°C.

Reference： [1] Patent: EP2952509, 2015, A1, . Location in patent: Paragraph 0043; 0044
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 2277,2280, 2281
[3] Journal of the American Chemical Society, 1977, vol. 99, p. 1172 - 1180
[4] Journal of the Chemical Society, 1963, p. 3523 - 3528
[5] Journal of Organic Chemistry, 1966, vol. 31, p. 631 - 632
[6] Patent: DE1009187, 1957, ,
[7] Patent: US2652402, 1952, ,

2
[ 85430-60-0 ]
[ 80-65-9 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 2277,2280, 2281
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 2277,2280, 2281
[3] Patent: US2652402, 1952, ,
[4] Patent: US2652402, 1952, ,

3
[ 497-25-6 ]
[ 80-65-9 ]

Reference： [1] Journal of the American Chemical Society, 1977, vol. 99, p. 1172 - 1180
[2] Organic Letters, 2005, vol. 7, # 13, p. 2767 - 2770

4
[ 109-84-2 ]
[ 616-38-6 ]
[ 80-65-9 ]

Reference： [1] MedChemComm, 2015, vol. 6, # 6, p. 1086 - 1092

5
[ 67-45-8 ]
[ 80-65-9 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 21, p. 4255 - 4261

6
[ 98025-70-8 ]
[ 80-65-9 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 3353

7
[ 80-65-9 ]
[ 698-63-5 ]
[ 67-45-8 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 2277,2280, 2281

[ 80-65-9 ] Synthesis Path-Downstream 1~88

1
[ 80-65-9 ]
[ 698-63-5 ]
[ 67-45-8 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2277,2280, 2281

2
[ 80-65-9 ]
[ 52661-56-0 ]
[ 3318-78-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2277,2280, 2281

3
[ 80-65-9 ]
[ 5275-69-4 ]
[ 3687-39-6 ]

Reference： [1]Patent: US2847416,1956,

4
[ 80-65-9 ]
[ 5275-71-8 ]
[ 112485-77-5 ]

Reference： [1]Latvijas PSR Zinatnu Akademijas Vestis,1959,p. 81,85
Chem.Abstr.,1959,p. 21862

5
[ 80-65-9 ]
[ 100-52-7 ]
[ 4341-14-4 ]

Reference： [1]Journal of the Chemical Society,1963,p. 3523 - 3528

6
[ 85430-60-0 ]
[ 80-65-9 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2277,2280, 2281
[2]Journal of the American Chemical Society,1955,vol. 77,p. 2277,2280, 2281
[3]Patent: US2652402,1952,
[4]Patent: US2652402,1952,

7
[ 98025-70-8 ]
[ 80-65-9 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1958,vol. 246,p. 3353

8
[ 109-84-2 ]
[ 105-58-8 ]
[ 80-65-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium methylate; for 4.0h;Reflux;	15.2g (0.2mol) 2-hydrazinoethanol (Intermediate 1), 31.0g (0.2mol) diethyl carbonate, and 3.0g (57mmol) sodium methoxide were added to a 100ml three-necked flask, and were refluxed for 4 hours, and after cooling, solids were precipitated, filtrated under vacuum, and dried. The solvent in the mother solution was removed by distillation. After column chromatography (eluent: methanol/dichloromethane (at a ratio of 1:20 by volume)), the obtained white solid and the dried solid were recrystallized in ethanol, to get 15.3g product (Intermediate 2), with a yield of 75%. 1H-NMR(400MHz,D2O)deltappm:4.33(2H,t,J=8.0Hz,J=8.0Hz),3.94(2H,s),3.70(2H,t,J= 4.0Hz,J=4.0Hz);EI-MS(m/z):103.1[M+H]+; m.p. 64-66C.
62.81%	With sodium methylate; for 4.0h;Reflux;	Initially, 2-hydrazine ethanol (22.80 g, 0.30 mol), diethyl carbonate(47.10 g, 0.39 mol), and sodium methoxide (4.50 g, 0.09 mol)were added into a 100 mL three-neck flask. The solutionwas heatedunder reflux for 4 h. After cooling to room temperature, the solid precipitate was filtered, and the solids were dried. The solvent wasevaporated to dryness. Column chromatography was performed onthe products (methanol/dichloromethane V/V, 1: 40). The whiteand dry solid was recrystallized with ethanol. The white solidweighed 19.22 g and provided a yield of 62.81%. 1H NMR (400 MHz,DMSO-d6) delta 4.67 (s, 2H), 4.32-4.20 (m, 2H), 2.65-2.57 (m, 2H); 13CNMR (DMSO-d6): delta 161.51, 62.61, 46.04. HRMS (ESI) m/z: calcd. forC3H6N2O2[M + H]+: 103.0508, found: 103.0504.

Reference： [1]Patent: EP2952509,2015,A1 .Location in patent: Paragraph 0043; 0044
[2]European Journal of Medicinal Chemistry,2020,vol. 194
[3]Journal of the American Chemical Society,1955,vol. 77,p. 2277,2280, 2281
[4]Journal of the American Chemical Society,1977,vol. 99,p. 1172 - 1180
[5]Journal of the Chemical Society,1963,p. 3523 - 3528
[6]Journal of Organic Chemistry,1966,vol. 31,p. 631 - 632
[7]Patent: DE1009187,1957,

9
[ 109-01-3 ]
[ 80-65-9 ]
[ 17481-62-8 ]
2-(4-methyl-piperazin-1-yl)-3-[(2-oxo-oxazolidin-3-ylimino)-methyl]-pyrido[1,2-a]pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1971,vol. 14,p. 913 - 915

10
[ 497-25-6 ]
[ 80-65-9 ]

Reference： [1]Journal of the American Chemical Society,1977,vol. 99,p. 1172 - 1180
[2]Organic Letters,2005,vol. 7,p. 2767 - 2770

11
[ 111-49-9 ]
[ 80-65-9 ]
[ 17481-62-8 ]
[ 36146-44-8 ]

Reference： [1]Journal of medicinal chemistry,1971,vol. 14,p. 913 - 915

12
[ 823-82-5 ]
[ 80-65-9 ]
[ 949-27-9 ]

Reference： [1]Journal of the Chemical Society,1964,p. 4730 - 4734

13
[ 80-65-9 ]
[ 1623-88-7 ]
[ 833-95-4 ]

Reference： [1]Journal of the Chemical Society,1964,p. 4730 - 4734

14
[ 80-65-9 ]
[ 58928-54-4 ]
[ 58928-47-5 ]

Reference： [1]Journal of Medicinal Chemistry,1976,vol. 19,p. 729 - 731

15
[ 80-65-9 ]
[ 6327-67-9 ]
[ 6345-51-3 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 282 - 285

16
[ 80-65-9 ]
[ 50-00-0 ]
[ 10020-75-4 ]

Reference： [1]Journal of Organic Chemistry,1966,vol. 31,p. 631 - 632

17
[ 80-65-9 ]
[ 19611-63-3 ]
[ 18707-46-5 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 282 - 285

18
[ 80-65-9 ]
[ 13383-40-9 ]
[ 90323-37-8 ]

Reference： [1]Journal of Pharmacy and Pharmacology,1964,vol. 16,p. 663 - 669

19
[ 80-65-9 ]
[ 18711-28-9 ]
[ 16711-31-2 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 282 - 285

20
[ 80-65-9 ]
[ 18711-50-7 ]
[ 18711-55-2 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 282 - 285

21
[ 80-65-9 ]
[ 18711-27-8 ]
[ 16711-13-0 ]

Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 282 - 285

22
[ 80-65-9 ]
[ 17515-80-9 ]
[ 17515-69-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 95 - 100

23
[ 80-65-9 ]
[ 117-34-0 ]
[ 70298-81-6 ]

Reference： [1]Pharmazie,1979,vol. 34,p. 12 - 13

24
[ 80-65-9 ]
[ 17709-98-7 ]
[ 20922-51-4 ]

Reference： [1]Acta Chemica Scandinavica (1947),1968,vol. 22,p. 1898 - 1906

25
[ 80-65-9 ]
[ 3223-20-9 ]
[ 65043-10-9 ]

Reference： [1]Pharmazie,1977,vol. 32,p. 323 - 325

26
[ 80-65-9 ]
[ 368-39-8 ]
[ 113849-14-2 ]
[ 58928-46-4 ]

Reference： [1]Journal of Medicinal Chemistry,1976,vol. 19,p. 729 - 731

27
[ 80-65-9 ]
[ 567-19-1 ]
[ 65923-10-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1977,vol. 15,p. 720 - 726

28
[ 80-65-9 ]
[ 91-56-5 ]
[ 95060-43-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1641 - 1645

29
[ 80-65-9 ]
[ 586-96-9 ]
[ 59478-02-3 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1526 - 1528
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1679 - 1681
[2]Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.),1992,vol. 41,p. 1400 - 1413
Izvestiya Akademi Nauk, Seriya Khimicheskaya,1992,p. 1804 - 1820

30
[ 80-65-9 ]
[ 552-89-6 ]
[ 19687-73-1 ]

Reference： [1]Xenobiotica,1994,vol. 24,p. 713 - 727
[2]Journal of the Chinese Chemical Society,2009,vol. 56,p. 581 - 588
[3]Journal of Agricultural and Food Chemistry,2017,vol. 65,p. 4255 - 4261
[4]Food Chemistry,2020,vol. 310

33
[ 98-01-1 ]
[ 80-65-9 ]
[ 860006-44-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

34
[ 14371-10-9 ]
[ 80-65-9 ]
[ 860006-45-7 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

35
[ 104-53-0 ]
[ 80-65-9 ]
[ 860006-46-8 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

36
[ 80-65-9 ]
[ 447-61-0 ]
3-[1-(2-Trifluoromethyl-phenyl)-meth-(E)-ylidene]-amino}-oxazolidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

37
[ 80-65-9 ]
[ 5470-84-8 ]
3-[4-Benzyloxy-but-(E)-ylideneamino]-oxazolidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

38
[ 80-65-9 ]
[ 104-87-0 ]
[ 860006-37-7 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

39
[ 80-65-9 ]
[ 104-88-1 ]
[ 860006-39-9 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

40
[ 80-65-9 ]
[ 89-98-5 ]
[ 860006-41-3 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

41
[ 80-65-9 ]
[ 66-77-3 ]
[ 860006-43-5 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

42
[ 80-65-9 ]
[ 100-52-7 ]
[ 860006-36-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

43
[ 80-65-9 ]
[ 123-11-5 ]
[ 860006-38-8 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

44
[ 80-65-9 ]
[ 529-20-4 ]
[ 860006-42-4 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

45
[ 80-65-9 ]
[ 6630-33-7 ]
[ 860006-40-2 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

46
[ 80-65-9 ]
[ 1123-56-4 ]
3-[1-(2,6-Dimethyl-phenyl)-meth-(E)-ylidene]-amino}-oxazolidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2767 - 2770

47
[ 158561-89-8 ]
[ 80-65-9 ]
3-benzenesulfonyl-5-chloro-1H-indole-2-carboxylic acid (2-oxo-oxazolidin-3-yl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3172 - 3184

48
[ 80-65-9 ]
[ 473257-46-4 ]
5-chloro-3-(3,5-dimethyl-benzenesulfonyl)-1H-indole-2-carboxylic acid (2-oxo-oxazolidin-3-yl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3172 - 3184

49
[ 80-65-9 ]
[ 491-37-2 ]
[ 7732-18-5 ]
[ 67863-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; isopropyl alcohol;	EXAMPLE I 3-[(4-Chromanylidene)amino]-2-oxazolidinone A 62-g (0.61 mole) portion of <strong>[80-65-9]3-amino-2-oxazolidinone</strong> was charged in a 500-ml, 3-necked flask equipped with a thermometer, stirrer and reflux condenser, and treated successively with 92 ml of H2 O, 8 ml of 10% HCl and 42 g (0.28 mole) of 4-chromanone in 200 ml ethanol. The reaction mixture was refluxed for 36 hr, stripped in vacuo to one-half volume and cooled in the refrigerator overnight. The slurry was filtered and the white crystalline solid washed with 50 ml of isopropanol then 200 ml of ether and dried. M.p. 105-108. Yield: 44 g (68%). The filtrate was extracted with 250 ml of CHCl3, and the CHCl3 extract dried over MgSO4, filtered, and stripped in vacuo.
	With hydrogenchloride; In ethanol; isopropyl alcohol;	A. 3-[(4-Chromanylidene)amino]-2-oxazolidinone A 62 g (0.61 mole) portion of <strong>[80-65-9]3-amino-2-oxazolidinone</strong> was charged in a 500 ml, 3-necked flask equipped with a thermometer, stirrer and reflux condenser, and treated successively with 92 ml of H2 O, 8 ml of 10% HCl and 42 g (0.28 mole) of 4-chromanone in 200 ml of ethanol. The reaction mixture was refluxed for 36 hrs., stripped in vacuo to one-half volume and cooled in the refrigerator overnight. The slurry was filtered and the white crystalline solid washed with 50 ml of isopropanol then 200 ml of ether and dried; m.p. 105-108. Yield: 44 g (68%). The filtrate was extracted with 250 ml of CHCl3, and the CHCl3 extract dried over MgSO4, filtered and stripped in vacuo.

Reference： [1]Patent: US4093627,1978,A
[2]Patent: US4108862,1978,A

50
[ 80-65-9 ]
isopropyl alcohol hydrogen chloride [ No CAS ]
[ 5802-17-5 ]
3-[(6-methoxy-4-chromanylidene)amino]-2-oxazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
115 g (73%)	In isopropyl alcohol; benzene;	EXAMPLE II 3-[(6-Methoxy-4-chromanylidene)amino]-2-oxazolidinone A solution of 62 g (0.61 mole) of 3-amino-2-oxazolidone in 650 ml of benzene was treated with 15 drops of HCl (isopropanol) solution using mechanical stirring, and refluxed until all water was removed via a Dean-Stark trap. The solution was then treated with 107 g (0.60 mole) of 6-methoxy-4-chromanone and refluxed for 11.5 hr. A 9.6 ml portion of water (theory: 10.8 ml) was collected. The reaction mixture was stripped of benzene under the water pump. The residue was taken up in 200 ml of 1:1 isopropanol:ether, stored 24 hr at room temperature, refrigerated overnight and filtered. The resultant cream-colored solid was washed with 125 ml of isopropanol, ether, and dried. M.p. 54-64; yield: 115 g (73%). The crude product was recrystallized from 340 ml of isopropanol (Darco), washed with 75 ml of isopropanol, ether and dried. M.p. 67-71; Yield: 88 g (56%). Anal. Calcd. for C13 H14 N2 O4: C, 59.53; H, 5.38; N, 10.68. Found: C, 59.57; H, 5.28; N, 10.56.

Reference： [1]Patent: US4093627,1978,A

51
[ 80-65-9 ]
isopropyl alcohol hydrogen chloride [ No CAS ]
[ 68043-53-8 ]
[ 67863-82-5 ]

Yield	Reaction Conditions	Operation in experiment
107 g (88%)	In nitromethane; benzene;	EXAMPLE III 3-[(6-Nitro-4-chromanylidene)amino]-2-oxazolidinone An 85 g (0.44 mole) portion of 6-nitro-4-chromanone in 460 ml of benzene was treated with 1 ml of HCl (isopropanol) solution, using mechanical stirring, and refluxed until all water was removed via a Dean-Stark trap. The solution was then treated with 46 g (0.46 mole) of <strong>[80-65-9]3-amino-2-oxazolidinone</strong> and refluxed for 2.6 hr. A 7.9 ml portion of water was collected (theory: 7.9 ml). The reaction mixture was filtered hot, cooled to 10-11 for 3 hrs. and filtered. The orange crystalline solid was washed with 100 ml of benzene, ether and dried, m.p. 168-170. Yield: 107 g (88%). The product was recrystallized from 650 ml of nitromethane (Darco), washed with 100 ml of cold nitromethane, ether and dried, m.p. 170-171, Yield: 84 g (69%). Anal. Calcd. for C12 H11 N3 O5: C, 51.99; H, 4.00; N, 15.16. Found: C, 51.96; H, 4.03; N, 15.14.

Reference： [1]Patent: US4093627,1978,A

52
[ 80-65-9 ]
[ 880473-81-4 ]
[ 951779-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 3.0h;Heating / reflux;	Example 8; Preparation of Compound 35; N-(4-chloro-2-propionylphenyl)-trifluoromethanesulfonamide (2.50 g, 7.9 mmol) and <strong>[80-65-9]3-amino-2-oxazolidinone</strong> (1.225 g, 11.85 mmol) were mixed in toluene (30 mL). The reaction was heated, with a Dean-Stark apparatus to remove water, at reflux for 3 hrs. The reaction mixture was cooled and evaporated to dryness. The residue was purified on a silica column using 20-100% CH2Cl2/PE, followed by 2% MeOH/DCM as solvent. The product was then recrystallized from DCM/PE to give 2.20 g of white solid. M.p. 115-117 C. 1H n.m.r. (CDCl3) delta 11.82, 1H, b; 7.69, 1H, d, J8.9 Hz; 7.60, 1H, d, J2.2 Hz; 7.42, 1H, dd, J18.9 Hz, J22.3 Hz; 4.54, 2H, t, J7.4 Hz; 3.96, 2H, t, J7.4 Hz; 2.93, 2H, q, J7.6 Hz; 1.13, 3H, t, J7.6 Hz.

Reference： [1]Patent: US2007/238700,2007,A1 .Location in patent: Page/Page column 32
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 649 - 652

53
[ 80-65-9 ]
[ 619-66-9 ]
[ 1013312-35-0 ]

Reference： [1]Chinese Chemical Letters,2010,vol. 21,p. 1049 - 1052
[2]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 1525 - 1531

54
[ 80-65-9 ]
[ 66-99-9 ]
[ 1195735-60-4 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 1752 - 1759

55
[ 80-65-9 ]
[ 880473-75-6 ]
[ 951779-31-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 649 - 652

56
[ 1026983-94-7 ]
[ 80-65-9 ]
C₁₇H₃₀N₂O₅ [ No CAS ]

Reference： [1]MedChemComm,2015,vol. 6,p. 1086 - 1092

57
[ 80-65-9 ]
[ 141-75-3 ]
C₄-3-aminooxazolidinone [ No CAS ]

Reference： [1]MedChemComm,2015,vol. 6,p. 1086 - 1092

58
[ 109-84-2 ]
[ 616-38-6 ]
[ 80-65-9 ]

Reference： [1]MedChemComm,2015,vol. 6,p. 1086 - 1092

59
[ 80-65-9 ]
[ 403-43-0 ]
4-fluoro-N-(2-oxo-oxazolidin-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In water; at 20℃;	[Example 1] 4-fluoro-N-(2-oxo-oxazolidin-3-yl)benzamide (Compound 1) 0.5g (4.9mmol) <strong>[80-65-9]3-amino oxazolidinone</strong> was put in a 25ml three-necked flask, 10ml water was added, and 0.92g (5.9mmol) 4-fluorobenzoyl chloride was added slowly dropwise at room temperature, the reactiong system was stirred overnight. White precipitate was precipitated, filtrated under vacuum, and recrystallized in ethanol to get white solid (Compound 1) 0.61g, with a yield of 56%. 1H-NMR(400MHz,DMSO)deltappm:10.87(1H,s),7.97(2H,t,J=4.0Hz,J=4.0Hz),7.40 (2H,t,J=8.0Hz,J=12.0Hz),4.46(2H,t,J=8.0Hz,J=8.0Hz), 3.79(2H,t,J=8.0Hz,J=8.0Hz); EI-MS(m/z):225.1[M+H]+; m.p.189-192C.

Reference： [1]Patent: EP2952509,2015,A1 .Location in patent: Paragraph 0045; 0046

60
[ 80-65-9 ]
[ 111-36-4 ]
1-(2-oxo-oxazolidin-3-yl)-3-butyl urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In 1,2-dimethoxyethane; for 0.75h;Reflux;	0.5g (4.9mmol) <strong>[80-65-9]3-amino oxazolidinone</strong> was put in a 25 ml three-necked flask, 10ml 1,2-dimethoxyethane was added, and 1.2g (5.9mmol) n-butyl isocyanate was slowly added dropwise, and then after 30 mins, white solid was precipitated, and the mixture was heated under refluxing for 15 mins, filtrated under vacuum, and recrystallized in isopropanol, to get 0.61g white solid (Compound 15), with a yield of 62%. 1H-NMR(400MHz,DMSO)deltappm:8.01(1H,s),6.69(1H,s),4.30(2H,t,J=8.0Hz,J=8.0Hz ),3.59(2H,t,J=8.0Hz,J=8.0Hz),3.00(2H,m),1.37(2H,m),1.25(2H,m),0.87(3H,m);EI-MS( m/z): 202.2[M+H]+; m.p. 98-100C.

Reference： [1]Patent: EP2952509,2015,A1 .Location in patent: Paragraph 0073; 0074

61
[ 80-65-9 ]
[ 459-04-1 ]
2-(4-fluorophenyl)-N-(2-oxo-oxazolidin-3-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine; In dichloromethane; at 0 - 20℃;	0.5g (4.9mmol) <strong>[80-65-9]3-amino oxazolidinone</strong> (Intermediate 2) was added to a 50ml three-necked flask, 25ml dichloromethane and 0.75g (7.4mmol) triethylamine were added, and 1.0g (5.9mmol) 2-(4-fluorophenyl) acetyl chloride was slowly added dropwise at 0C in an ice bath, and then the mixture was stirred at room temperature overnight, the solvent was distilled under reduced pressure, and the residue was recrystallized in ethanol, to get 0.52g white solid (Compound 31), with a yield of 45%. 1H-NMR(400MHz,DMSO)deltappm:10.41(1H,s),7.30(2H,t,J=4.0Hz,J=8.0Hz),7.17(2H, t,J=8.0Hz,J=8.0Hz),4.35(2H,t,J=8.0Hz,J=8.0Hz),3.65(2H,t,J=8.0Hz,J=8.0Hz),3.49(2H, s);EI-MS(m/z): 239.2[M+H]+; m.p. 131-134C.

Reference： [1]Patent: EP2952509,2015,A1 .Location in patent: Paragraph 0105; 0106

62
[ 80-65-9 ]
2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)benzoyl chloride [ No CAS ]
2-fluoro-N-(2-oxooxazolidin-3-yl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃;	To a screw-cap vial containing <strong>[80-65-9]3-aminooxazolidin-2-one</strong> (0.05 g) suspended in CH2CI2 (12 mL) cooled to 0 C. Then triethylamine (0.14 mL) was introduced followed by 2-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzoyl chloride (0.15 g) in one portion. The reaction contents were then poured into a separatory funnel and diluted with CH2CI2 and water. The organic layer was separated and thenwashed with 1 N HCI, 1 N NaOH, and brine. The solvent was removed under reduced pressure and the crude residue was purified by flash chromatography over silica gel (heptane:ethyl acetate gradient) togive the title compound as a white solid (mp: 186- 189C). 1H NMR (400 MHz, CDCI3): oe 8.60 (d, 1H),8.32 (d, 1H), 8.10 (d, 1H), 7.97 (d, 1H), 4.55 (t, 2H), 4.00 (t, 2H). LC/MS retention time = 0.85 minutes,361 (M+H)

Reference： [1]Patent: WO2017/157962,2017,A1 .Location in patent: Page/Page column 60; 61

63
[ 80-65-9 ]
[ 94193-36-9 ]
C₁₄H₁₅N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.32 g	In methanol; at 60 - 70℃; for 2.0h;	(b) 0.5 g (2.0 mmol) of Compound II was dissolved in 10 ml of methanol, 0.24 g (2.4 mmol) of Furazolidone metabolites <strong>[80-65-9]AOZ</strong>, at 60 ~ 70 reaction 2h, the reaction was completed, cooled to room temperature, filtered to give 0.32g furazolidone metabolite haptens. The structural formula III of the hapten and the synthetic route thereof are shown in FIG. 1.

Reference： [1]Patent: CN106866568,2017,A .Location in patent: Paragraph 0048; 0049; 0052; 0054; 0055

64
[ 67-45-8 ]
[ 80-65-9 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2017,vol. 65,p. 4255 - 4261

65
[ 80-65-9 ]
(R)-3-benzyloxy-2-butanone [ No CAS ]
C₁₄H₁₈N₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3723 - 3727

66
[ 80-65-9 ]
C₁₇H₁₂N₂O₁₀ [ No CAS ]
C₂₈H₂₉N₇O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
475 mg	In methanol; at 60℃; for 1.5h;	(3) 500 mg (1.2 mmol) of Compound IV was dissolved in 10 ml of methanol,Add 247 mg (2.4 mmol) of the furazolidone metabolite <strong>[80-65-9]AOZ</strong>,After reacting at 60 C for 1.5 h or more, the reaction is completed and cooled to room temperature.Filtration, the furazolidone metabolite hapten V-<strong>[80-65-9]AOZ</strong> 475mg,The mass spectrum of V-<strong>[80-65-9]AOZ</strong> is shown in Figure 2.

Reference： [1]Patent: CN108530373,2018,A .Location in patent: Paragraph 0055; 0059

67
[ 80-65-9 ]
[ 57597-64-5 ]
DAOC-AOZ [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 2649 - 2657

68
[ 80-65-9 ]
[ 66-25-1 ]
3-(hexylidene)amino-2-oxazolidinone [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8290 - 8294

69
[ 80-65-9 ]
[ 78-84-2 ]
3-(2-methylpropylidene)amino-2-oxazolidinone [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8290 - 8294

70
[ 80-65-9 ]
[ 630-19-3 ]
3-(2,2-dimethylpropylidene)amino-2-oxazolidinone [ No CAS ]