Trifluoroacetic acid → HCID 86637595, compound

HRID 1694341Notes

Reaction equation

HRID 1694341 reaction equation
C(OC([NH:8][NH:9][C:10](=[S:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O)(C)(C)C.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].C1(SC)C=CC=CC=1>C(Cl)Cl>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][NH2:8])=[S:18])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 866375961,1-Dimethylethyl 2-[(4-fluorophenyl)thioxomethyl]hydrazinecarboxylate

Product 1

HCID 86637595HCID 86637595, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic salt. To a solution of N′-(4-fluoro-thiobenzoyl)-hydrazinecarboxylic acid tert-butyl ester (1.97 mmol) in CH2Cl2 is added trifluoroacetic acid (3 mL) and thioanisole (2.7 mmol). The mixture is stirred at room temperature for 1 hour. After evaporation of the solvent the mixture is purified by automated column chromatography (hexanes/EtOAc) to yield 4-fluoro-thiobenzoic acid hydrazide trifluoroacetic acid salt: 1H NMR (400 MHz, CDCl3) δ 9.5 (bs, 3H), 7.8-7.76 (m, 2H), 7.05 (t, J=8.4 Hz, 2H); LC/MS: (ES+) 171 (M+1)+.

Workup

  1. customAfter evaporation of the solvent the mixture
  2. customis purified by automated column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-4ffe454f05bc4842b87275a51510b733
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

Loading…