Benzoyl chloride, 3,4,5-trimethoxy- → 3,4,5-trimethoxy-N-methylbenzamide

HRID 235532Notes

Reaction equation

HRID 235532 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[CH:16]([N:19](C(C)C)CC)(C)C.Cl.CN>O1CCCC1>[CH3:16][NH:19][C:6](=[O:7])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1

Participants

5

Reactant 3

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochloride

Product 1

HCID 8205143,4,5-trimethoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 3,4,5-trimethoxybenzoyl chloride) (2.9 g, 17.0 mmol) and tetrahydrofuran (170 mL) and cool to 0° C. Add diisopropylethylamine (5.92 mL, 34 mmol). Add methylamine hydrochloride (1.26 g, 18.7 mmol). Allow to stir for 1 hour and concentrate in vacuo. Chromatograph on silica gel eluting sequentially with 50% ethyl acetate/hexane to give N-methyl-3,4,5-trimethoxybenzamide: TLC Rf =0.45 (silica gel, 50% ethyl acetate/hexane).

Workup

  1. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-2b75909f078d47f99a1e6a227db82441
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

Loading…