Dichloromethane → 4-Phenylbutanethioamide

HRID 1378604Notes

Reaction equation

HRID 1378604 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([NH2:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1.CCCCCC.C(Cl)Cl>C1(C)C=CC=CC=1.C(O)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([NH2:12])=[S:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 87949Lawesson's reagentHCID 2633634-phenylbutanamide

Product 1

HCID 222823784-PhenylbutanethioamideYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-phenylbutyramide (0.373 g, 2.28 mmol) in toluene (15 mL) was added Lawesson's reagent (0.461 g, 1.14 mmol). The reaction was refluxed overnight, cooled to room temperature and concentrated yielding an orange oil. Flash chromatography of this oil (1:1 hexane:methylene chloride with 1% acetic acid) yielded 4-phenylthiobutyramide (0.184 g) as a white solid: 1HNMR (DMSO d6 ) 400 mHz 9.33 (s, 1 H), 9.13 (s, 1 H), 7.29-7.23 (m, 2 H), 7.20-7.15 (m, 3 H), 2.56 (t, J=7.58 Hz, 2 H), 2.50-2.42 (m, 2 H), 2.00-1.85 (m, 2 H).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. concentrationconcentrated
  3. customyielding an orange oil

Sources & evidence

ORD record
ord-e3ca98cc7da242a19e85566293cd2f8e
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

Loading…