Acetyl chloride → HCID 10543259, compound

HRID 636470Notes

Reaction equation

HRID 636470 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:18]([O-:20])=[O:19])=[C:11]([CH:15]=[CH:16][CH:17]=1)[NH:12][CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>ClCCl>[C:28]([N:12]([CH2:13][CH3:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[N+:18]([O-:20])=[O:19])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10707324HCID 10707324, compound

Product 1

HCID 10543259HCID 10543259, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzyloxy-N-ethyl-2-nitroaniline (2.20 g) and triethylamine (1.23 g) in dichloromethane (21 ml) was added acetyl chloride (698 mg) under ice-cooling, and the mixture was stirred for 3 hours at ambient temperature. The reaction mixture was washed with water, saturated sodium bicarbonate solution, water and brine successively, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel flash chromatography (dichloromethane - ethyl acetate) to give N-acetyl-3-benzyloxy-N-ethyl-2-nitroaniline (1.71 g).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with water, saturated sodium bicarbonate solution, water and brine successively
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel flash chromatography (dichloromethane - ethyl acetate)

Sources & evidence

ORD record
ord-13a77542febb427498448a33427b013b
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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