Dichloromethane → 3-Phenylpropanethioamide

HRID 1378606Notes

Reaction equation

HRID 1378606 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([NH2:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1.CCCCCC.C(Cl)Cl>C1(C)C=CC=CC=1.C(O)(=O)C>[C:1]1([CH2:7][CH2:8][C:9]([NH2:11])=[S:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 76253-PhenylpropanamideHCID 8058HexaneHCID 87949Lawesson's reagent

Product 1

HCID 51507353-PhenylpropanethioamideYield 23.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3-phenylpropionamide (1.653 g, 6.827 mmol) in toluene (20 mL) was added Lawesson's reagent (0.716 g, 1.77 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 3-phenylthiopropionamide (0.070 g) as a white solid: mp 82°-83° C.; 1HNMR (DMSO d6) 300 mHz 9.35 (br s, 1 H), 9.15 (br s, 1 H), 7.34-7.10 (m, 2 H), 2.95 (t, J=8.48 Hz, 2 H), 2.72 (t, J=8.48 Hz, 2 H).

Workup

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

Sources & evidence

ORD record
ord-7dec5218e5674c959072d8306e0cf727
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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