Triethylamine → HCID 89444767, compound

HRID 1522777Notes

Reaction equation

HRID 1522777 reaction equation
[C:1]([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:29])/[CH:14]=[C:15](\[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[CH3:30])([CH3:4])([CH3:3])[CH3:2].C(O)(=[S:34])C.C(N(CC)CC)C>C(N(CC)CC)C.ClCCl>[C:1]([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:29])[CH2:14][C:15]([SH:34])([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:19])[F:18])=[CH:9][C:8]=1[CH3:30])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89444764HCID 89444764, compoundHCID 178418634HCID 178418634, compound2×

Product 1

HCID 89444767HCID 89444767, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2-Methyl-4-[(E)-4,4,4-trifluoro-3-(3,4,5-trichloro-phenyl)-but-2-enoyl]-benzoic acid tert-butyl ester (1.29 g) was added thioacetic acid (6 eq.) and triethylamine (12 μL). The solution was stirred under argon at room temperature for 24 hours. More thioacetic acid (1 mL) and triethylamine (1 drop) were added and the solution was stirred under argon at room temperature for 72 hours. To this mixture was added a minimum of dichloromethane and then isolute. The suspension 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 (573 mg).

Workup

  1. stirringthe solution was stirred under argon at room temperature for 72 hours
  2. customThe suspension was evaporated under vacuo
  3. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-e9dab21445194f909645ca0f9ac01824
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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