Pyridine → N-(4-chloro-5-formylthiazol-2-yl)benzamide

HRID 45318Notes

Reaction equation

HRID 45318 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[S:12][C:13]([CH:17]=[O:18])=[C:14]([Cl:16])[N:15]=1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:16][C:14]1[N:15]=[C:11]([NH:10][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:12][C:13]=1[CH:17]=[O:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 110301542-Amino-4-chloro-1,3-thiazole-5-carbaldehyde

Product 1

HCID 86642515N-(4-chloro-5-formylthiazol-2-yl)benzamideYield 19%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl chloride (1.25 mL, 10.70 mmol) was added to a solution of 2-amino-4-chlorothiazole-5-carbaldehyde (1.63 g, 10.00 mmol), pyridine (79.10, 12.30 mmol) and 4-dimethylaminopyridine (10 mg) in tetrahydrofuran (100 mL) at 0° C. The reaction mixture was stirred at ambient temperature overnight and then concentrated. Purification of the residue by column chromatography afforded N-(4-chloro-5-formylthiazol-2-yl)benzamide in 19% yield (0.52 g); 1H NMR (CDCl3, 300 MHz) δ 10.0 (s, 1H), 8.28-7.45 (m, 5H); MS (ES+) m/z 267.1 (M+1).

Workup

  1. concentrationconcentrated
  2. customPurification of the residue by column chromatography

Sources & evidence

ORD record
ord-88645f12d72249b992767196277d92ef
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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