Hydrazine → 4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid hydrazide

HRID 2103424Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH3:27])=[CH:6][CH:5]=1.[NH2:29][NH2:30]>CO.O>[CH3:27][C:13]1[N:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=2)[S:16][C:12]=1[CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:29][NH2:30])=[O:2])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid methyl ester (Example 6, 364 mg, 1 mmol) in methanol (10 mL) add anhydrous hydrazine (128 ml, 4 mmol). Warm the resulting mixture to 60° C. and stir at this temperature for 18 hrs. Cool the resulting solution to room temperature, and add 3 drops of water. Concentrate the solution under vacuum and purify the residue by flash chromatography (elute with 5% methanol in dichloromethane) to give the title compound (271 mg).

Workup

temperatureCool the resulting solution to room temperature
concentrationConcentrate the solution under vacuum
custompurify the residue
washby flash chromatography (elute with 5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-9d06103d98f44a9bb466130cbd4b5965
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576109B2

Reaction notes

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