Pyridine → 2-Chloro-2-phenyl-n-[4-(thiazol-2-ylsulfamoyl)-phenyl]-acetamide

HRID 219552

Reaction equation

HRID 219552 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([S:8]([NH:11][C:12]2[S:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:2]=1.N1C=CC=CC=1.[Cl:23][CH:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:25](Cl)=[O:26]>C(Cl)Cl>[Cl:23][CH:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:25]([NH:7][C:6]1[CH:1]=[CH:2][C:3]([S:8](=[O:10])(=[O:9])[NH:11][C:12]2[S:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:5]=1)=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5340SulfathiazoleHCID 102902Chloro(phenyl)acetyl chloride

Product 1

HCID 579363832-Chloro-2-phenyl-n-[4-(thiazol-2-ylsulfamoyl)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized according to general procedure 1: N′-(2-thiazolyl)sulfanilamide (5.60 g, 22 mmol), pyridine (3.6 mL, 44 mmol), 2-chloro-2-phenyl acetylchloride (3.8 mL, 26.4 mmol, 1.2 equiv) in DCM (400 mL). Yield: 6.73 g (75%) of a white solid. 1H-NMR (DMSO-d6) δ 10.85 (s, 1H), 7.78-7.72 (m, 4H), 7.60-7.57 (m, 2H), 7.45-7.37 (m, 3H), 7.25 (d, J=4.6 Hz, 1H), 6.82 (d, J=4.6 Hz, 1H), 5.77 (s, 1H). LC/MS (10-99%) M/Z: M+1 obs=408.1; tR=2.61 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e28b7e6f4ec3452ebdef22d257a7808d
Source dataset
uspto-grants-2012_06
Patent number
US08202861B2

Linked notes

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