1-(p-Chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochloride → 1-(p-Chlorobenzyl)-alpha,alpha-dimethyl-5-fluoro-3-methylthioindole-2-propanoic acid

HRID 483415Notes

Reaction equation

HRID 483415 reaction equation
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)N)=[CH:5][CH:4]=1.C[O:20][C:21](=[O:31])[C:22]([CH3:30])([CH3:29])[CH2:23][C:24](=O)[CH2:25][S:26][CH3:27]>>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:10]3[C:15](=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[C:25]([S:26][CH3:27])=[C:24]2[CH2:23][C:22]([CH3:30])([CH3:29])[C:21]([OH:31])=[O:20])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 145912421-(p-Chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochlorideHCID 15035406Methyl 2,2-dimethyl-5-methylthio-4-oxopentanoate

Product 1

HCID 150353871-(p-Chlorobenzyl)-alpha,alpha-dimethyl-5-fluoro-3-methylthioindole-2-propanoic acid

Procedure

Following the procedure of Example 10, but using 1-(p-chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochloride and methyl-2,2-dimethyl-5-methylthio-4-oxopentanoate as starting materials and hydrolysis at reflux, the title compound was prepared, mp 161°-163°.

Workup

  1. custommaterials and hydrolysis
  2. temperatureat reflux

Sources & evidence

ORD record
ord-edea355ae4f64b468d061603a0d0fc87
Source dataset
uspto-grants-1993_07
Patent number
US05225421

Reaction notes

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