Water → HCID 20329024, compound

HRID 2052063Notes

Reaction equation

HRID 2052063 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)([O:3]CC)=[O:2].[C-:25]#[N:26].[K+].[C:28](=[O:31])([O-])[O-].[NH4+:32].[NH4+].[OH2:34]>[OH-].[Na+].CN(C=O)C>[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=1[C:13]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:32][C:25](=[O:34])[NH:26][C:28]1=[O:31])([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 20329021HCID 20329021, compound

Product 1

HCID 20329024HCID 20329024, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 17.8 g (0.06 mol) of 2-(4-carboxybutoxy)-benzophenone (17), 4.15 g (0.064 mol) of potassium cyanide, 17.3 g (0.18 mol) of ammonium carbonate, 24 ml of H2O, and 200 ml of DMF was placed in a steel autoclave and heated to 110° C. for 5 days. The autoclave was cooled and the contents dissolved in 800 ml of 10% aqueous sodium hydroxide solution. It was washed with two 400 ml portions of ether and acidified to pH 4.5 with 6 N hydrochloric acid. A precipitate occurred that was filtered and dried to give 24.6 g of 5-[2-(4-carboxybutoxy)-phenyl]-5-phenylhydantoin (18). Two recrystallizations from aqueous methanol gave a white solid, mp 231°-232° C.

Workup

  1. temperatureThe autoclave was cooled
  2. washIt was washed with two 400 ml portions of ether
  3. filtrationthat was filtered
  4. customdried

Sources & evidence

ORD record
ord-6126388a7b0f47489b25a03f35d4bfd8
Source dataset
uspto-grants-1980_01
Patent number
US04182856

Reaction notes

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