1-Hydroxybenzotriazole → 3-methoxy-N-methoxy-N-methyl-4-(trifluoromethyl)benzamide

HRID 1375017Notes

Reaction equation

HRID 1375017 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:11]([OH:13])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:11]([N:3]([O:4][CH3:5])[CH3:2])=[O:13]

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 179641303-Methoxy-4-(trifluoromethyl)benzoic acid

Product 1

HCID 179640593-methoxy-N-methoxy-N-methyl-4-(trifluoromethyl)benzamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,O-Dimethylhydroxylamine hydrochloride (5.37 g) was added to a mixture of 3-methoxy-4-(trifluoromethyl)benzoic acid (11.0 g), 1-hydroxybenzotriazole (6.76 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.59 g) and N,N-diisopropylethylamine (9.6 ml) in dichloromethane (200 ml), and the whole was stirred at room temperature for 18 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture and the organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with 25% of ethyl acetate in hexane as an eluent to give 3-methoxy-N-methoxy-N-methyl-4-(trifluoromethyl)-benzamide (12.0 g) as a colorless oil.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel with 25% of ethyl acetate in hexane as an eluent

Sources & evidence

ORD record
ord-2fece65c791d457cb6819080d892090d
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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