Water → 2-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid ethyl ester

HRID 1785477Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Cl)=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2].[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20][CH:19]=1.[Li]N([Si](C)(C)C)[Si](C)(C)C.O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=[CH:19]2)=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-chloro-4-phenylthiazole-5-carboxylic acid ethyl ester (134 mg, 0.5 mmol), benzimidazole (Aldrich) (73.8 mg, 0.625 mmol) and LiN(TMS)2 (1N tetrahydrofuran solution, 0.63 ml) in tetrahydrofuran (2 ml) was heated in a micro-wave oven at 120° C. for 30 min. Water (3 ml) was added and the mixture was filtered, washed with water and ethyl acetate, dried in air flow to give 2-(benzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid ethyl ester (108 mg, 61%). The aqueous solution was concentrated to remove tetrahydrofuran and then extracted with ethyl acetate to recover an additional amount of the product (100 mg, 75% pure). 1H-NMR (CDCl3) 8.84 (s, 1H); 8.16 (d, 1H); 7.81-7.90 (m, 3H); 7.39-7.58 (m, 5H); 4.37 (q, 2H); 1.27 (t, 3H). MS M/z 350 (M+1).

Workup

filtrationthe mixture was filtered
washwashed with water and ethyl acetate
customdried in air flow

Sources & evidence

ORD record: ord-c9ff6485c25c4a798f1ff4bd86c8e00b
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504513B2

Reaction notes

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