Benzamide → HCID 10998364, compound

HRID 1707804Notes

Reaction equation

HRID 1707804 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][CH:12](OC)[CH2:13][Cl:14]>ClCCl>[CH3:10][O:11][CH:12]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][Cl:14]

Participants

4

Reactant 2

HCID 2331Benzamide2×HCID 609862-Chloro-1,1-dimethoxyethane

Product 1

HCID 10998364HCID 10998364, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

9.6 g of benzamide and 49.8 g of chloroacetaldehyde dimethyl acetal, and an amount of strongly acidic ion exchanging resin having an exchange capacity corresponding to the benzamide were agitated for 3 hours at a temperature of 60° C. The reaction fluid was cooled to 40° C., and 30 ml of dichloromethane was added thereto. The ion exchanging resin was removed by filtration under reduced pressure, and the dichloromethane and excess chloroacetaldehyde dimethyl acetal were removed from the filtrate by vacuum distillation, 100 ml of hexane was added thereto and crystals were precipitated, and these were then filtered and desiccated to obtain 7.0 g of compound (1).

Workup

  1. temperatureThe reaction fluid was cooled to 40° C.
  2. customThe ion exchanging resin was removed by filtration under reduced pressure
  3. customthe dichloromethane and excess chloroacetaldehyde dimethyl acetal were removed from the filtrate by vacuum distillation, 100 ml of hexane
  4. additionwas added
  5. customcrystals were precipitated
  6. filtrationthese were then filtered

Sources & evidence

ORD record
ord-325fca7eec70452291fb1230e3b0e6c0
Source dataset
uspto-grants-1994_10
Patent number
US05354905

Reaction notes

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