Dichloromethane → 4-(4-Bromophenyl)butanethioamide

HRID 1378581Notes

Reaction equation

HRID 1378581 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:13])=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1.CCCCCC.C(Cl)Cl>C1(C)C=CC=CC=1.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:13])=[S:23])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 87949Lawesson's reagentHCID 44177354-(4-Bromophenyl)butanamide

Product 1

HCID 541321334-(4-Bromophenyl)butanethioamideYield 22.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-(4-bromophenyl)butyramide (1.653 g, 6.827 mmol) in toluene (35 mL) was added Lawesson's reagent (1.381 g, 3.414 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-(4-bromophenyl) thiobutyramide as off-white needles (0.196 g): mp 104°-105° C. 1H NMR (DMSO-d6) 300 mHz δ9.33 (br s, 1H), 9.12 (br s, 1H), 7.44 (d, J=8.11 Hz, 2H), 7.14 (d, J=8.48 H z, 2H), 2.56-2.41 (m, 4H), 1.95-1.85 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-777398cd28d34a6ea7704877434bc80f
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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