Diphenyl sulfide → HCID 18183657, compound

HRID 1358165Notes

Reaction equation

HRID 1358165 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[C:21]([C:11]1[CH:10]=[CH:9][C:8]([S:7][C:1]2[CH:2]=[CH:3][C:4]([C:21](=[O:22])[CH2:20][CH2:19][CH3:18])=[CH:5][CH:6]=2)=[CH:13][CH:12]=1)(=[O:22])[CH2:20][CH2:19][CH3:18]

Participants

5

Reactant 3

HCID 8766Diphenyl sulfideHCID 8855Butyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18183657HCID 18183657, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diphenylsulfide (33.3 ml, 0.20 mol) is added to a suspension of AlCl3 (54.7 g, 0.41 mol) in 350 ml of CH2Cl2. n-Butyryl chloride (41.4 ml, 0.40 mol) is added dropwise slowly in an ice bath and the reaction solution is stirred at room temperature for 15 h. Then, the reaction solution is poured into ice-water. The crude product is extracted with CH2Cl2, washed with 1N NaOH and brine, dried over MgSO4, and concentrated. The product is obtained as a white solid. 1H NMR (CDCl3), δ[ppm]: 1.00 (t, 6H), 1.77 (tq, 4H), 2.92 (t, 4H), 7.40 (d, 4H), 7.90 (d, 4H).

Workup

  1. extractionThe crude product is extracted with CH2Cl2
  2. washwashed with 1N NaOH and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product is obtained as a white solid

Sources & evidence

ORD record
ord-0c6a096b3e084de9ac07c37388e2f499
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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