Carbon Disulfide → HCID 10808337, compound

HRID 1873122Notes

Reaction equation

HRID 1873122 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:22](Cl)(=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.C(=S)=S>O>[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[C:14]=1[C:22]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:31])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 127581572-Benzyl-1-benzothiophene

Product 1

HCID 10808337HCID 10808337, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tin tetrachloride (9.0 mL, 76.91 mmol) was added dropwise over a 25 minute period to a stirred solution of 2-benzyl-benzo[b]thiophene (14.87 g, 96.79 mmol), p-anisoyl chloride (11.75 g, 68.87 mmol) and carbon disulfide (75 mL) under a dry nitrogen atmosphere. After 6 hours, the reaction mixture was added to water and extracted with dichloromethane. The dichloromethane extract was washed with sat. aq. sodium bicarbonate and brine. The solvent was removed and the resultant solid was triturated with pet. ether to give the title compound as a white solid (20.2 g, 85%): mp 135-137° C.: NMR (CDCl3); δ 7.85 (dm, J=9 Hz, 2H), 7.73 (dm, 1H), 7.42 (dm, 1H), 7.18-7.30 (m, 7H), 6.93 (dm, J=9 Hz, 2H), 4.21 (s, 2H, CH2), 3.88 (s, 3H, CH3): IR (KBr, cm-1): 1650; MS (EI): 358 (100%, MI), 343 (15%), 327 (75%); Anal. Calc. for C23H18O2S: C, 77.07, H, 5.06, N, 0.00. Found: C, 76.91, H, 5.02, N, -0.12.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe dichloromethane extract
  3. washwas washed with sat. aq. sodium bicarbonate and brine
  4. customThe solvent was removed
  5. customthe resultant solid was triturated with pet. ether

Sources & evidence

ORD record
ord-fa3680001aff47209802089ab11fa2cc
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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