Acetyl chloride → HCID 67326585, compound

HRID 1910799Notes

Reaction equation

HRID 1910799 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][CH:6]([CH3:23])[C:7](=[O:22])[CH2:8][NH:9][C:10]([CH3:21])([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[CH3:11].C(N(CC)CC)C>C(Cl)Cl>[CH3:21][C:10]([N:9]([CH2:8][C:7](=[O:22])[CH:6]([CH3:5])[CH3:23])[C:1](=[O:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67106782HCID 67106782, compound

Product 1

HCID 67326585HCID 67326585, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.24 mL, 3.4 mmol) was added to an ice-cooled solution of 3-methyl-1-[1-methyl-1-(3-nitro-phenyl)-ethylamino]-butan-2-one (600 mg, 2.27 mmol) and triethylamine (0.79 mL, 5.6 mmol) in DCM (10 mL). The mixture was maintained between 0 and 5° C. for 30 min. then concentrated in vacuo. The residue was redissolved in ethyl acetate, washed with water then brine and dried over sodium sulfate. Concentration afforded N-[1-methyl-1-(3-nitro-phenyl)-ethyl]-N-(3-methyl-2-oxo-butyl)-acetamide (620 mg, 89%) as an oil.

Workup

  1. temperatureThe mixture was maintained between 0 and 5° C. for 30 min.
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was redissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialbrine and dried over sodium sulfate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-1e140c9e81bf496db88cd1a2b81661ed
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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