4-Chlorobutyronitrile → HCID 21279795, compound

HRID 543754Notes

Reaction equation

HRID 543754 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[NH:7]1[CH:14]=[CH:13][C:11]([NH2:12])=[N:10][C:8]1=[S:9]>CCO.[OH-].[Na+]>[NH2:12][C:11]1[CH:13]=[CH:14][N:7]=[C:8]([S:9][CH2:2][CH2:3][CH2:4][C:5]#[N:6])[N:10]=1

Participants

5

Reactant 2

HCID 123364-Chlorobutyronitrile2×HCID 178507915HCID 178507915, compound

Product 1

HCID 21279795HCID 21279795, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Chlorobutyronitrile (0.23 g.) in EtOH (2 ml.) was added to a solution of 2-thiocytosine (0.25 g.) in 0.5 N aqueous NaOH (5 ml.) and the mixture stirred for 18 hours. A further portion of 4-chlorobutyronitrile (0.23 g.) was added and the mixture stirred a further 24 hours. The solution was concentrated in vacuo to 2 ml. and cooled and the crystalline precipitate collected to give 4-[4-aminopyrimid-2-ylthio]butyronitrile (0.3 g.), m.p. 99°-100°.

Workup

  1. stirringthe mixture stirred a further 24 hours
  2. concentrationThe solution was concentrated in vacuo to 2 ml
  3. temperatureand cooled
  4. customthe crystalline precipitate collected

Sources & evidence

ORD record
ord-62a36339d4bb4a9a8bf8c7948f745c01
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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