Triethylamine → HCID 13503382, compound

HRID 485253Notes

Reaction equation

HRID 485253 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:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].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:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 13371112HCID 13371112, compound

Product 1

HCID 13503382HCID 13503382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 20.0 g. of bis(4-chlorophenyl)acryloyl chloride in 150 m. of dichloromethane is added to a stirred solution of 10.3 g. of methyl 2-aminobenzoate and 12.2 ml. of triethylamine in 150 ml. of dichloromethane. This solution is stirred under reflux for 3 hours, then overnight at room temperature, and evaporated. The residue is stirred with 300 ml. of boiliing acetone, filtered white hot, and chilled. The resulting solid is collected and dried in vacuo, giving 15.6 g. of the desired product as a white solid, m.p. 141°-143° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customovernight at room temperature, and evaporated
  3. stirringThe residue is stirred with 300 ml
  4. filtrationof boiliing acetone, filtered white hot
  5. temperaturechilled
  6. customThe resulting solid is collected
  7. customdried in vacuo
  8. customgiving 15.6 g

Sources & evidence

ORD record
ord-917225b1843c425c88297c28e670da3f
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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