N,N-Diphenylcarbamic chloride → HCID 53870652, compound

HRID 1975393Notes

Reaction equation

HRID 1975393 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])=[CH:4][CH:3]=1.[C:23]1([N:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1.C(OCC)(=O)C>[C:23]1([N:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30](=[O:31])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 65741N,N-Diphenylcarbamic chlorideHCID 53838801HCID 53838801, compound

Product 1

HCID 53870652HCID 53870652, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.4 g of methyl 6-(4-aminophenyl)-6-(3-pyridyl)-hex-5-enoate and 2.1 g of N,N-diphenyl-carbamoylchloride is stirred in 25 ml of pyridine for 18 hours at ambient temperature. The solvent is eliminated and the residue is taken up in ethyl acetate. The organic phase is washed with water, dried and evaporated down. The residue is saponified in a mixture of 20 ml of ethanol and 6 ml of 4N sodium hydroxide solution for 30 minutes at 50° C. The reaction solution is diluted with water and extracted with ethyl acetate. Then the aqueous phase is neutralised by the addition of citric acid, the precipitate formed is suction filtered and recrystallised from ethyl acetate/isopropanol.

Workup

  1. washThe organic phase is washed with water
  2. customdried
  3. customevaporated down
  4. additionThe residue is saponified in a mixture of 20 ml of ethanol and 6 ml of 4N sodium hydroxide solution for 30 minutes at 50° C
  5. additionThe reaction solution is diluted with water
  6. extractionextracted with ethyl acetate
  7. additionThen the aqueous phase is neutralised by the addition of citric acid
  8. customthe precipitate formed
  9. filtrationfiltered
  10. customrecrystallised from ethyl acetate/isopropanol

Sources & evidence

ORD record
ord-92fa9475182d437187f59dd0e1b9b336
Source dataset
uspto-grants-1994_02
Patent number
US05286736

Reaction notes

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