Water → 4-Amino-beta-(4-chlorophenyl)-3,5-dichloro-cinnamic acid morpholide

HRID 580604Notes

Reaction equation

HRID 580604 reaction equation
C(OP([CH2:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])(OCC)=O)C.[H-].[Na+].[NH2:20][C:21]1[C:35]([Cl:36])=[CH:34][C:24]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=O)=[CH:23][C:22]=1[Cl:37].O>O1CCCC1>[NH2:20][C:21]1[C:22]([Cl:37])=[CH:23][C:24]([C:25]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[CH:9][C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[O:11])=[CH:34][C:35]=1[Cl:36]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11207805Phosphonic acid, [2-(4-morpholinyl)-2-oxoethyl]-, diethyl esterHCID 133733144-Amino-3,4',5-trichlorobenzophenone

Product 1

HCID 545219194-Amino-beta-(4-chlorophenyl)-3,5-dichloro-cinnamic acid morpholide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5.3 g (0.02 mol) of diethylphosphonoacetic acid morpholide in 100 ml of dry tetrahydrofuran was slowly added dropwise, while stirring, to a suspension of 1 g of sodium hydride (0.02 mol, 50% in oil) in 50 ml of dry tetrahydrofuran. Slight heating and strong foaming occurred. After all had been added, the mixture was stirred for 10 minutes more. A solution of 3 g (0.01 mol) of 4-amino-3,4',5-trichlorobenzophenone in 20 ml of dry tetrahydrofuran was added dropwise to the resulting clear solution, and the mixture was heated for 16 hours at reflux temperature. After cooling, the solution was poured into water, and the aqueous mixture was extracted exhaustively with methylene chloride. The methylene chloride phase was dried with sodium sulfate and evaporated by evaporation in vacuo. The residue was crystallized from isopropanol/petroleum ether. The colorless crystals thus obtained, melting point 150°-155° C., contained the cis/trans isomers in a ratio of 1:3.

Workup

  1. temperatureSlight heating
  2. additionAfter all had been added
  3. temperaturethe mixture was heated for 16 hours
  4. temperatureat reflux temperature
  5. temperatureAfter cooling
  6. extractionthe aqueous mixture was extracted exhaustively with methylene chloride
  7. dry with materialThe methylene chloride phase was dried with sodium sulfate
  8. customevaporated by evaporation in vacuo
  9. customThe residue was crystallized from isopropanol/petroleum ether
  10. customThe colorless crystals thus obtained

Sources & evidence

ORD record
ord-d3a7eb78bd444d0fb967eeb28ced0d84
Source dataset
uspto-grants-1988_06
Patent number
US04753934

Reaction notes

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