Potassium Cyanide → 5-(4-Cyanophenyl)-5-(9H-thioxanthen-9-ylmethyl)hydantoin

HRID 442804Notes

Reaction equation

HRID 442804 reaction equation
[CH:1]1[C:14]2[CH:13]([CH2:15][C:16]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:26](=[O:29])([O-])[O-].[NH4+:30].[NH4+:31].[C-]#N.[K+].[CH2:35]([OH:37])C.O>>[C:22]([C:21]1[CH:20]=[CH:19][C:18]([C:16]2([CH2:15][CH:13]3[C:14]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[S:6][C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[NH:31][C:35](=[O:37])[NH:30][C:26]2=[O:29])=[CH:25][CH:24]=1)#[N:23]

Participants

5

Reactant 4

HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 19096565Water ethanolHCID 700925354-[2-(9H-thioxanthen-9-yl)acetyl]benzonitrile

Product 1

HCID 536856165-(4-Cyanophenyl)-5-(9H-thioxanthen-9-ylmethyl)hydantoin

Procedure

Following the procedure described in Example (v) using 4-[2-(9H-thioxanthen-9-yl)acetyl]benzonitrile (3 g, 8.8 mmol), ammonium carbonate (3.1 g, 3.2 mmol) and potassium cyanide (1.03 g, 5.8 mmol) in ethanol-water (1:1, 15 ml) gave after work up a yellow solid. This was purified on flash silica eluting with dichloromethane and then ethyl acetate. The ethyl acetate fractions were combined and evaporated to a solid which was triturated with dichloromethane to give 5-(4-cyanophenyl)-5-(9H-thioxanthen-9-ylmethyl) hydantoin as a yellow solid.

Workup

  1. customgave after work up a yellow solid
  2. customThis was purified on flash silica eluting with dichloromethane
  3. customevaporated to a solid which
  4. customwas triturated with dichloromethane

Sources & evidence

ORD record
ord-a31d3bfe61324803afb1c5cae553927f
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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