4-Methylmorpholine → 4-bromo-2-chloro-N-methoxy-N-methylbenzamide

HRID 561968Notes

Reaction equation

HRID 561968 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([Cl:11])[CH:3]=1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[CH3:31][NH:32][O:33][CH3:34].C(N(CC)CC)C>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:32]([O:33][CH3:34])[CH3:31])=[O:7])=[C:4]([Cl:11])[CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 598430764-bromo-2-chloro-N-methoxy-N-methylbenzamideYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-2-chloro-benzoic acid (3.30 g, 14 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (2.44 g, 14 mmol) and N-methylmorpholine in tetrahydrofuran were stirred for 2 hours at room temperature. N,O-Dimethylhydroxyamine hydrochloride (1.37 g, 14 mmol) and triethylamine (2 mL, 14 mmol) were added and the resulting mixture was stirred for 3 days. The reaction mixture was evaporated and ethyl acetate was added. The mixture was washed with 1N aqueous hydrochloric acid, water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 4-bromo-2-chloro-N-methoxy-N-methyl-benzamide (3.52 g, 91%).

Workup

  1. customThe reaction mixture was evaporated
  2. additionethyl acetate was added
  3. washThe mixture was washed with 1N aqueous hydrochloric acid, water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e37ec6363d7a4630818008638747dc37
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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