Triethylamine → HCID 13503381, compound

HRID 485252Notes

Reaction equation

HRID 485252 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:9][C:10](Cl)=[O:11])=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:9][C:10]([NH:20][C:21]2[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 13371112HCID 13371112, compound

Product 1

HCID 13503381HCID 13503381, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 20.0 g. of bis(4-chlorophenyl)acryloyl chloride in 150 ml. of dichloromethane is added to a stirred solution of 10.3 g. of methyl 3-aminobenzoate and 12.2 ml. of triethylamine in 150 ml. of dichloromethane. This solution is stirred under reflux for 3 hours and then at room temperature overnight and evaporated. The residue is stirred with 300 ml. of boiling acetone, filtered white hot, and the filtrate is chilled. The resulting solid is collected and dried in vacuo, giving 13.8 g. of the desired product as a white solid, m.p. 155°-159° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customat room temperature overnight and evaporated
  3. stirringThe residue is stirred with 300 ml
  4. filtrationof boiling acetone, filtered white hot
  5. temperaturethe filtrate is chilled
  6. customThe resulting solid is collected
  7. customdried in vacuo
  8. customgiving 13.8 g

Sources & evidence

ORD record
ord-63243316e3db4dfcac373472e7c63e67
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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