Phenyl isocyanate → HCID 21187980, compound

HRID 1383440Notes

Reaction equation

HRID 1383440 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[C:12]([OH:14])=O.[OH-].[K+]>O>[CH3:25][N:24]([CH2:23][CH2:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:11]1[NH:10][C:8](=[O:9])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]1=[O:14])[CH3:26]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 14797Potassium HydroxideHCID 21187997HCID 21187997, compound

Product 1

HCID 21187980HCID 21187980, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.4 ml of phenyl isocyanate are slowly added to a solution of 4 g of 2-amino-2-{[2(N,N-dimethylamino)ethyl]oxy-phenyl}-acetic acid and 1.65 g of potassium hydroxide in water (about 20 ml). The mixture is stirred for 12 hours at ambient temperature, filtered, acidified with aqueous HCl solution (10%) (about pH 2) and refluxed. After 6 hours it is slowly cooled and made alkaline with aqueous Na2CO3 solution (10%). The precipitate obtained is recrystallised from ethyl acetate. 3 g of the title compound are obtained in the form of a white solid (melting point: 120-124° C.).

Workup

  1. filtrationfiltered
  2. temperaturerefluxed
  3. temperatureAfter 6 hours it is slowly cooled
  4. customThe precipitate obtained
  5. customis recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-6ecc1a5e98904ae5b3d4f7076d160f30
Source dataset
uspto-grants-2001_07
Patent number
US06255327B1

Reaction notes

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