Potassium Cyanide → HCID 53772933, compound

HRID 442800Notes

Reaction equation

HRID 442800 reaction equation
C(C1C=CC([C:9](=[O:26])[CH2:10][CH2:11][CH:12]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:19][C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)=C(C)C=1)#N.[C-:28]#[N:29].[K+].[C:31](=[O:34])([O-])[O-].[NH4+:35].[NH4+:36]>C(O)C.O>[C:28]([C:15]1[CH:16]=[CH:17][C:18]([C:10]2([CH2:11][CH:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[O:19][C:20]4[C:25]3=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:36][C:31](=[O:34])[NH:35][C:9]2=[O:26])=[C:13]([CH3:12])[CH:14]=1)#[N:29]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 54215258HCID 54215258, compound

Product 1

HCID 53772933HCID 53772933, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 1-(4-cyano-2-methylphenyl)-2-(9H-xanthen-9-ylmethyl)ethanone (6.3 g, 18.6 mmol), potassium cyanide (2.2 g, 33.4 mmol) and ammonium carbonate (6.42 g, 66.9 mmol) in ethanol (9 ml) and water (9 ml) was heated at 85° C. for 2 days and then 100° C. for 3 days and finally 120° C. for 1 day in a teflon lined stainless steel sealed tube. The reaction was worked up as in Example 1 (v) to give a red oil. Purification on flash silica eluting with ethyl acetate-hexane (2:3 then 1:1 then 3:2) gave 5-(4-cyano-2-methylphenyl)-5-(9H-xanthen-9-ylmethyl)hydantoin as a pale yellow solid, m.p. 148°-152° C.

Workup

  1. customto give a red oil
  2. customPurification on flash silica eluting with ethyl acetate-hexane (2:3

Sources & evidence

ORD record
ord-5066cb7659d249a4a8e66156d47d78ce
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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