HCID 89444805, compound → HCID 89444767, compound

HRID 1522780Notes

Reaction equation

HRID 1522780 reaction equation
[C:1]([O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:33])[CH2:14][C:15]([S:29]C(=O)C)([C:20]2[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[CH3:34])([CH3:4])([CH3:3])[CH3:2]>NC1C=CC=CC=1>[C:1]([O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:33])[CH2:14][C:15]([SH:29])([C:20]2[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=2)[C:16]([F:17])([F:18])[F:19])=[CH:9][C:8]=1[CH3:34])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 89444805HCID 89444805, compound

Product 1

HCID 89444767HCID 89444767, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6115AnilineSolvent

Procedure

A solution of 4-[3-Acetylsulfanyl-4,4,4-trifluoro-3-(3,4,5-trichloro-phenyl)-butyryl]-2-methyl-benzoic acid tert-butyl ester (1.33 g) in aniline (13 mL) was stirred at room temperature for 3 hours. The mixture was quenched with a solution of hydrochloric acid (1N), extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane) to give 2-Methyl-4-[4,4,4-trifluoro-3-mercapto-3-(3,4,5-trichloro-phenyl)-butyryl]-benzoic acid tert-butyl ester (950 mg).

Workup

  1. customThe mixture was quenched with a solution of hydrochloric acid (1N)
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe collected organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated under vacuo
  7. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-a291e730eb1a44438741d886c5f98f23
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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