Hydrochloric Acid → HCID 70077434, compound

HRID 343932Notes

Reaction equation

HRID 343932 reaction equation
[CH2:1]([S:8][C:9]1[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+].[C:22](=[O:25])([O-])[O-].[NH4+:26].[NH4+:27].Cl.[CH2:29]([OH:31])C.O>>[CH2:1]([S:8][C:9]1[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:10]=1[CH:11]1[NH:27][C:29](=[O:31])[NH:26][C:22]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 19096565Water ethanolHCID 53923823HCID 53923823, compound

Product 1

HCID 70077434HCID 70077434, compound

Conditions

Temperature
85 °C

Procedure

A mixture of 2-benzylthio-4-cyanobenzaldehyde (1.38 g, 5 mmol), potassium cyanide (0.78 g, 12 mmol) and ammonium carbonate (2.304 g, 24 mmol) in ethanol-water (1:1, 16 ml) was heated with stirring in a sealed reaction vessel at 85° C. for 16 hours. The resulting cooled solution was acidified with 2N hydrochloric acid (6 ml), then extracted with ethyl acetate (3×10 ml), dried and evaporated to a pale brown solid. Chromatography on flash silica eluting with ether/hexane 4:1 gave 5-(2-benzylthio-4-cyanophenyl)hydantoin as a pale orange solid.

Workup

  1. temperaturewas heated
  2. temperatureThe resulting cooled solution
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. customdried
  5. customevaporated to a pale brown solid

Sources & evidence

ORD record
ord-9acbead8196d4495a3f26636fafbf82e
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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