Triethylamine → HCID 22117812, compound

HRID 1740446Notes

Reaction equation

HRID 1740446 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](O)=[O:6].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.[CH3:32][NH:33][O:34][CH3:35]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([N:33]([O:34][CH3:35])[CH3:32])=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27355443-Bromo-4-chlorobenzoic acid

Product 1

HCID 22117812HCID 22117812, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 10.0 g of 3-bromo-4-chlorobenzoic acid in 275 ml of anhydrous dichloromethane at 0° C. were added 7.6 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.5 ml of triethylamine followed by 3.9 g of N,O-dimethylhydroxylamine hydrochloride. After stirring overnight at room temperature the mixture was washed with 200 ml of water and then with 200 ml of a 1M solution of hydrochloric acid. The organic solution was dried over anhydrous sodium sulphate and concentrated under reduced pressure to give 10.7 g of 3-bromo-4-chloro-N-methoxy-N-methylbenzamide as a cream solid.

Workup

  1. washwas washed with 200 ml of water
  2. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10a0a14282b74af380643b34c9cf6e5d
Source dataset
uspto-grants-1999_10
Patent number
US05969139

Reaction notes

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