Hydrochloric Acid → 5-(4-Cyano-2-phenoxyphenyl)hydantoin

HRID 343935Notes

Reaction equation

[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)#[N:2].[C-]#N.[K+].[C:21](=[O:24])([O-])[O-].[NH4+:25].[NH4+:26].Cl.[CH2:28]([OH:30])C.O>O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[NH:26][C:28](=[O:30])[NH:25][C:21]2=[O:24])=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 4-cyano-2-phenoxybenzaldeyde (2.23 g, 10 mmol), potassium cyanide (1.30 g, 20 mmol) and ammonium carbonate (3.84 g, 40 mmol) in ethanol-water (30 ml, 1:1) was heated to 80° C. for 2 hours in a sealed vessel. The mixture was diluted with water (30 ml), cautiously acidified to pH1 with 5M hydrochloric acid (20 ml) and extracted with ethyl acetate (30 ml). The extracts were washed with water (30 ml), dried, filtered and evaporated to a viscous brown oil (3.1 g). Chromatography on flash silica (graded elution with 2 to 4% methanol in dichloromethane) gave 5-(4-cyano-2-phenoxyphenyl)hydantoin as a yellow foam.

Workup

extractionextracted with ethyl acetate (30 ml)
washThe extracts were washed with water (30 ml)
customdried
filtrationfiltered
customevaporated to a viscous brown oil (3.1 g)

Sources & evidence

ORD record: ord-a8d3db47a04a4cb486bfe1bf6134c96a
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863947

Reaction notes

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