p-Acetanisidide, alpha,alpha,alpha-trifluoro- → HCID 86689275, compound

HRID 409334Notes

Reaction equation

HRID 409334 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=O)[CH3:12])=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1COCC1>[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[S:25])[CH3:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 74437p-Acetanisidide, alpha,alpha,alpha-trifluoro-HCID 87949Lawesson's reagent

Product 1

HCID 86689275HCID 86689275, compoundYield 173%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-(trifluoromethoxy)phenyl)acetamide (112 g, 0.511 mol) was dissolved in THF (400 ml) and Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) (100 g, 0.247 mol) was added. The suspension was stirred at rt for 3 days, then filtered, filtrate evaporated and the residue was purified by chromatography (20% EtOAc in hexane) to give 100.5 g (84%) of N-(4-(trifluoromethoxy)phenyl)ethanethioamide.

Workup

  1. filtrationfiltered
  2. customfiltrate evaporated
  3. customthe residue was purified by chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-16a9c6e0e42c4585b3a3d2230596eba8
Source dataset
uspto-grants-2014_06
Patent number
US08759382B2

Reaction notes

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