Acetyl chloride → ethyl N-acetyl-o-chlorobenzimidate

HRID 2350935Notes

Reaction equation

HRID 2350935 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)Cl>[C:20]([N:8]=[C:4]([O:5][CH2:6][CH3:7])[C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[Cl:1])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13092607Ethyl 2-chlorobenzimidate

Product 1

HCID 19847831ethyl N-acetyl-o-chlorobenzimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 41 g (22.3 mmol) of ethyl o-chlorobenzimidate and 25 g (25 mmol) of triethylamine in 500 ml of methylene chloride is treated dropwise with 19.5 g (24.8 mmol) of acetyl chloride, the temperature being held at 40° C. by the use of cooling. The reaction mixture is stirred at room temperature for a further 30 minutes, and the mixture is then washed in sequence with water, 5% sodium bicarbonate solution and semi-saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After distillation of the crude product at 110° C./0.16 mmHg (21.33 Pa) there is obtained ethyl N-acetyl-o-chlorobenzimidate as a colourless liquid.

Workup

  1. custombeing held at 40° C. by the use
  2. temperatureof cooling
  3. washthe mixture is then washed in sequence with water, 5% sodium bicarbonate solution and semi-saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. distillationAfter distillation of the crude product at 110° C./0.16 mmHg (21.33 Pa) there

Sources & evidence

ORD record
ord-8122371c8b494cef9db30a2314216a50
Source dataset
uspto-grants-1989_10
Patent number
US04871757

Reaction notes

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