Ammonium Carbonate → 5-(4-Cyano-2-(2-phenylethylthio)phenyl)hydantoin

HRID 343929Notes

Reaction equation

[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([S:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:4]=1)#[N:2].[C:20](=[O:23])([O-])[O-].[NH4+:24].[NH4+:25].[CH2:26]([OH:28])C.O>O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[NH:25][C:26](=[O:28])[NH:24][C:20]2=[O:23])=[C:5]([S:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 4-cyano-2-(2-phenylethylthio)benzaldehyde (2.14 g, 8 mmol) potassium cyanide (1.04 g, 16 mmol) and ammonium carbonate (3.07 g, 32 mmol) in ethanol-water (1:1, 20 ml) was heated to 80° C. for 2 hours in a sealed pressure vessel. The cooled solution was diluted with water (30 ml) to precipitate a sticky solid, filtered, washed with water and triturated with CHCl3 (20 ml) to give 5-(4-cyano-2-(2-phenylethylthio)phenyl)hydantoin, m.p. 198° C.

Workup

customto precipitate a sticky solid
filtrationfiltered
washwashed with water
customtriturated with CHCl3 (20 ml)

Sources & evidence

ORD record: ord-2fda19b55403423ab27abf5168fd9e00
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863947

Reaction notes

Loading…