Triethylamine → N-methoxy N-methyl 2-(phenylthio)-benzamide

HRID 1706598Notes

Reaction equation

HRID 1706598 reaction equation
[C:1]1([S:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][NH:18][O:19][CH3:20].C(N(CC)CC)C>O1CCCC1>[CH3:20][O:19][N:18]([CH3:17])[C:10](=[O:11])[C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 2913222-(Phenylsulfanyl)benzoyl chloride

Product 1

HCID 20333643N-methoxy N-methyl 2-(phenylthio)-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.7 parts of 2-(phenylthio)-benzoylchloride in 50 parts of tetrahydrofuran was added to a cold (~5°) stirred solution of 1 part N,O-dimethyl hydroxylamine and 1.6 parts triethylamine in 75 parts of tetrahydrofuran. The mixture was stirred for 8 hrs. and the temperature was allowed to rise to room temperature. Removal of the precipitated triethylamine hydrochloride by filtration and concentration of the filtrate under vacuum gave 3.3 parts of N-methoxy N-methyl 2-(phenylthio)-benzamide as a very viscous oil. NMR (CDCl3) 3.3δ(S,3H,N-CH3), 3.5δ(S,3H,-O-CH3), 7.3δ(m,9H,Aromatic H).

Workup

  1. customto rise to room temperature
  2. customRemoval of the precipitated triethylamine hydrochloride
  3. filtrationby filtration and concentration of the filtrate under vacuum

Sources & evidence

ORD record
ord-8e667d8f305647b4902c4648bc60ceae
Source dataset
uspto-grants-1980_06
Patent number
US04208205

Reaction notes

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