Lawesson's reagent → N,N-Diethyl-3-fluorobenzenecarbothioamide

HRID 368590Notes

Reaction equation

HRID 368590 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>>[CH2:1]([N:3]([CH2:13][CH3:14])[C:4](=[S:24])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 963334N,N-diethyl-3-fluorobenzamide

Product 1

HCID 18630340N,N-Diethyl-3-fluorobenzenecarbothioamideYield 142%

Procedure

A mixture of N,N-diethyl-3-fluorobenzamide (4.69 g, 24 mmol) (cf Mills, et al., "Directed Ortho Metalation of N,N-Diethylbenzamides. Silicon Protection of Ortho Sites and the o-Methyl Group," J. of Organic Chemistry 54: 4372-4385, 1989), Lawesson's reagent (6.47 g, 16 mmol) and xylenes (150 mL) was refluxed overnight, then was concentrated and kugelrohr distilled (105-110° C. at 0.25 torr) to yield 4.8 g N,N-diethyl-3-(fluoro)thiobenzamide as a yellow oil, a 95% yield.

Workup

  1. concentrationwas concentrated
  2. distillationkugelrohr distilled (105-110° C. at 0.25 torr)

Sources & evidence

ORD record
ord-5ac82d765988430595bf51e996352acf
Source dataset
uspto-grants-2000_10
Patent number
US06133252

Reaction notes

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