Phosphorus sulfide (P2S5) → HCID 86722576, compound

HRID 1503789Notes

Reaction equation

HRID 1503789 reaction equation
[F:1][C:2]([F:40])([F:39])[CH:3]([C:30]1[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=1)/[CH:4]=[CH:5]/[C:6]1[CH:25]=[CH:24][C:9]([C:10]([NH:12][C:13]2([C:16](=O)[NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:15][CH2:14]2)=[O:11])=[C:8]([C:26]([F:29])([F:28])[F:27])[CH:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:42].C[Si](C)(C)O[Si](C)(C)C>C(Cl)Cl>[F:1][C:2]([F:40])([F:39])[CH:3]([C:30]1[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=1)/[CH:4]=[CH:5]/[C:6]1[CH:25]=[CH:24][C:9]([C:10]([NH:12][C:13]2([C:16](=[S:42])[NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:15][CH2:14]2)=[O:11])=[C:8]([C:26]([F:29])([F:28])[F:27])[CH:7]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)2×HCID 24764Hexamethyldisiloxane2×HCID 86722577HCID 86722577, compound

Product 1

HCID 86722576HCID 86722576, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (E)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-N-(1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl)-2-(trifluoromethyl)benzamide (200 mg, 0.31 mmol) in CH2Cl2 (20 mL) was added P4S10 (34 mg, 0.155 mmol) and hexamethyldisiloxane (HMDO, 0.1 mL, 0.517 mmol) and the reaction mixture was refluxed for 4 h. The reaction mixture was cooled to room temperature and another portion of P4S10 (34 mg, 0.155 mmol) and HMDO (0.1 mL, 0.517 mmol) were added and the reaction mixture was refluxed for 16 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica (100-200 mesh) eluting with 10% EtOAc in hexane to give the title compounds as yellow gum (37 mg, 18%). Characterization data for this molecule is listed in Table 2.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. temperaturethe reaction mixture was refluxed for 16 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica (100-200 mesh)
  5. washeluting with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-ebdb71ef14a64051908fcdad8bcf61d1
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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