Benzoyl chloride → HCID 54371665, compound

HRID 2231155Notes

Reaction equation

HRID 2231155 reaction equation
[CH3:1][N:2]([CH3:21])[C:3](=[O:20])[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([OH:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13].C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCOCC>[CH3:21][N:2]([CH3:1])[C:3](=[O:20])[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([O:14][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67899397HCID 67899397, compound

Product 1

HCID 54371665HCID 54371665, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a well stirred mixture of 12.4 g of N,N-dimethylalphaethoxycarbonyl-beta-hydroxy-2,4-dichlorocinnamamide, 4.0 g of triethylamine and 150 ml of dry ether at 4° C. was added dropwise benzoyl chloride at such a rate that the temperature did not exceed 5° C. The reaction was allowed to warm up to room temperature, stirred at this temperature for 2 hours, the cooled again to 4° C. The solids were filtered off and the filtrate concentrated under reduced pressure to yield 12.0 g of a white solid. The solid was crystallized from ether/hexane to yield 8.0 g of the desired product, m.p. 106° C.

Workup

  1. customdid not exceed 5° C
  2. stirringstirred at this temperature for 2 hours
  3. temperaturethe cooled again to 4° C
  4. filtrationThe solids were filtered off
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-b399ce37341545d7b146e43fee194a53
Source dataset
uspto-grants-1988_11
Patent number
US04781750

Reaction notes

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