Phosphorus sulfide (P2S5) → HCID 21865382, compound

HRID 856991Notes

Reaction equation

HRID 856991 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=O)[C:7]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].C[Si](C)(C)O[Si](C)(C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[S:20])[C:7]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 24764HexamethyldisiloxaneHCID 99707112,8-Dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 21865382HCID 21865382, compoundYield 191.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2,8-dichloro-10,11-dihydro-dibenzo[a,d]cycloheptene-5-one (0.70 g, 2.53 mMol) in toluene (20 ml) were added phosphorus pentasulfide (1 eq, 561 mg) and hexamethyldisiloxane (1 eq, 0.54 ml). The mixture was heated 3 h at reflux and allowed to cool to room temperature. The mixture was filtered through a pad of silica gel (70 g) and washed through with 8:1 heptane/ethyl acetate. Evaporation of the solvent under reduced pressure afforded 2,8-dichloro-10,11-dihydro-dibenzo[a,d]cycloheptene-5-thione as a blue solid (710 mg, 95%) that was used without further purification.

Workup

  1. temperatureThe mixture was heated 3 h
  2. temperatureat reflux
  3. filtrationThe mixture was filtered through a pad of silica gel (70 g)
  4. washwashed through with 8:1 heptane/ethyl acetate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-68aa38c2f0aa42b080a0276da2d673dc
Source dataset
uspto-grants-2006_12
Patent number
US07144890B2

Reaction notes

Loading…