4-Chlorophenyl Isocyanate → 1-(4-Chloro-phenylcarbamoyl)-2,5-dihydro-1h-pyrrole-2-carboxylic acid

HRID 1674488Notes

Reaction equation

HRID 1674488 reaction equation
[CH2:1]1[NH:5][CH:4]([C:6]([OH:8])=[O:7])[CH:3]=[CH:2]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1>C([O-])(O)=O.[Na+]>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:5]2[CH2:1][CH:2]=[CH:3][CH:4]2[C:6]([OH:8])=[O:7])=[O:18])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 978583,4-Dehydroproline

Product 1

HCID 673449501-(4-Chloro-phenylcarbamoyl)-2,5-dihydro-1h-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

0.250 g (2.21 mmol) 3,4-dehydro-DL-proline are dissolved in 15 ml of 5% NaHCO3 solution, combined with 0.678 ml (4.42 mmol) 4-chlorophenylisocyanate and stirred for 16 h at 80° C. Then the mixture is cooled, filtered and the residue is washed with water. The filtrate is adjusted to pH 1 with semi-concentrated HCl, extracted 2× with ethyl acetate, dried on sodium sulphate and concentrated i. vac.

Workup

  1. temperatureThen the mixture is cooled
  2. filtrationfiltered
  3. washthe residue is washed with water
  4. extractionextracted 2× with ethyl acetate
  5. customdried on sodium sulphate
  6. concentrationconcentrated i

Sources & evidence

ORD record
ord-1717675b400b48159c8b7f30983f0757
Source dataset
uspto-grants-2011_08
Patent number
US08003639B2

Reaction notes

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