4-Methylmorpholine → 4-bromo-N-methoxy-N,2-dimethylbenzamide

HRID 238400Notes

Reaction equation

HRID 238400 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.[CH3:41][NH:42][O:43][CH3:44]>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:42]([O:43][CH3:44])[CH3:41])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 189704854-bromo-N-methoxy-N,2-dimethylbenzamideYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of compound 4-bromo-2-methylbenzoic acid D-1 (50 g, 0.23 mol) in DCM (500 mL) was added EDCI (48 g, 0.25 mol), HOBt (34.1 g, 0.25 mol), NMM (50.5 g, 0.50 mol) and N,O-dimethylhydroxylamine hydrochloride (24.3 g, 0.25 mol). The reaction mixture was stirred at room temperature overnight, diluted with DCM, washed with H2O (300 mL), 1 N HCl (300 mL), and saturated sodium bicarbonate solution (300 mL), dried over sodium sulfate, and concentrated to give the desired product D-2 (55 g, yield 91.6%) as yellow oil.

Workup

  1. washwashed with H2O (300 mL), 1 N HCl (300 mL), and saturated sodium bicarbonate solution (300 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b8ce98ff65dd4b4d93cdb62d991571b3
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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