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Hydrazine → 4-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzoic Acid Hydrazide

HRID 1869286
Notes
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Reaction equation

HRID 1869286 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[S:16][C:17]=2[CH3:18])=[CH:6][CH:5]=1.[NH2:30][NH2:31]>CO.O>[CH3:18][C:17]1[S:16][C:15]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:14][C:13]=1[CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:30][NH2:31])=[O:2])=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 9321HydrazineHCID 579867424-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylethoxy]-benzoic acid methyl ester

Product 1

HCID 579867444-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzoic Acid HydrazideYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887Methanol
Solvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylethoxy]-benzoic acid methyl ester (Example 4, 410 mg, 1 mmol) in methanol (3 mL) add anhydrous hydrazine (0.32 ml, 10 mmol). Warm the resulting mixture to 60° C. and stir at this temperature for 66 hrs. Cool the resulting solution to room temperature, and add 3 drops of water. Filter the precipitate wash with ether to give the title compound (279 mg).

Workup

  1. temperatureCool the resulting solution to room temperature
  2. filtrationFilter the precipitate
  3. washwash with ether

Sources & evidence

ORD record
ord-a64a7aecce714671bc2e061c437095bb
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07638539B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes