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

HRID 2103424
Notes
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Reaction equation

HRID 2103424 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 9321HydrazineHCID 578043074-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid methyl ester

Product 1

HCID 578043044-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid hydrazideYield 66.5%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887Methanol
Solvent

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

  1. temperatureCool the resulting solution to room temperature
  2. concentrationConcentrate the solution under vacuum
  3. custompurify the residue
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes