Acetonitrile → HCID 19704886, compound

HRID 726952Notes

Reaction equation

HRID 726952 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)=[O:5])C.[C:12]1([CH2:18][O:19][C:20]2[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(#N)C>C(Cl)Cl>[C:12]1([CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([NH:11][C:8]3[S:9][CH:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]=3)=[O:25])=[CH:27][CH:28]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 19704886HCID 19704886, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-thiazolecarboxylic acid ethyl ester (6.85 g, 39.8 mmol) was allowed to react with 4-phenylmethoxybenzoyl chloride (10.72 g, 43.8 mmol) according to the procedure in Example 1. The reaction was completed in 18 hours. After workup and flash chromatography on silica gel eluting with 1-7% acetonitrile in methylene chloride, the ethyl ester of 2-[[4-phenylmethoxybenzoyl]amino]-4-thiazolecarboxylic acid was obtained (70% yield) and was hydrolyzed to the corresponding acid with 1.0N NaOH as described in Example 1.

Sources & evidence

ORD record
ord-a6e6a5b6264e489eb456f378e20ced8b
Source dataset
uspto-grants-1998_01
Patent number
US05712270

Reaction notes

Loading…