Lawesson's reagent → HCID 22346994, compound

HRID 897877Notes

Reaction equation

HRID 897877 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:27]2)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[S:27])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 531936HCID 531936, compound

Product 1

HCID 22346994HCID 22346994, compoundYield 178.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N1-(4-bromophenyl)-2-fluorobenzamide (3.3 g, 0.0112 mol) and 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (2.27 g, 0.00561 mol) was heated in toluene at reflux under an atmosphere of nitrogen for 3 hours. The reaction mixture was cooled to ambient temperature, the solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (1:6) as mobile phase to yield N1-(4-bromophenyl)-2-fluoro-1-benzenecarbothioamide (3.1 g, 0.010 mol) as a yellow solid.

Workup

  1. temperatureat reflux under an atmosphere of nitrogen for 3 hours
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-e632914176994e0e977e0c97a15fe7f0
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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