4-Chlorophenyl Isocyanate → 6-[3-(3-(4-Chlorophenyl)-ureido)-phenyl]-6-(3-pyridyl)-hex-5-enoic acid

HRID 1975392Notes

Reaction equation

HRID 1975392 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>O1CCCC1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:32])[NH:1][C:2]2[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 53766536Methyl 6-(3-aminophenyl)-6-(3-pyridyl)hex-5-enoate

Product 1

HCID 545606926-[3-(3-(4-Chlorophenyl)-ureido)-phenyl]-6-(3-pyridyl)-hex-5-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.4 g of methyl 6-(3-aminophenyl)-6-(3-pyridyl)-hex-5-enoate and 1.5 g of 4-chlorophenylisocyanate are stirred in 50 ml of tetrahydrofuran at ambient temperature for one hour. The reaction mixture is evaporated down, the residue is mixed with water and extracted with ethyl acetate/ethanol (9:I). The organic phase is evaporated down and the residue is saponified in 60 ml of ethanol and 6 ml of 4N sodium hydroxide solution at 50° C. for one hour. The reaction mixture is evaporated down, the residue is taken up in 100 ml of water and extracted with ethyl acetate. The aqueous phase is neutralised by the addition of citric acid, whereupon the product is precipitated. The precipitate is suction filtered, washed with water and diisopropylether and recrystallised from ethyl acetate/diisopropylether.

Workup

  1. customThe reaction mixture is evaporated down
  2. additionthe residue is mixed with water
  3. extractionextracted with ethyl acetate/ethanol (9:I)
  4. customThe organic phase is evaporated down
  5. customThe reaction mixture is evaporated down
  6. extractionextracted with ethyl acetate
  7. additionThe aqueous phase is neutralised by the addition of citric acid, whereupon the product
  8. customis precipitated
  9. filtrationfiltered
  10. washwashed with water and diisopropylether
  11. customrecrystallised from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-69588ffccb5b48d1ba263fa09cb32810
Source dataset
uspto-grants-1994_02
Patent number
US05286736

Reaction notes

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