tert-Butyl isothiocyanate → HCID 54198371, compound

HRID 2309723Notes

Reaction equation

HRID 2309723 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[N:3]=1.[C:14]([N:18]=[C:19]=[S:20])([CH3:17])([CH3:16])[CH3:15].C([Li])CCC>C1COCC1.CCCCCC>[C:14]([NH:18][C:19](=[S:20])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[N:3]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 11544tert-Butyl isothiocyanateHCID 21279726HCID 21279726, compoundHCID 178418339Butyllithium

Product 1

HCID 54198371HCID 54198371, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 4-(2-aminopyrid-6-ylthio)butyronitrile (0.39 g.) and t-butylisothiocyanate (0.25 g.) in THF (10 ml.) was stirred under an argon atmosphere while adding a solution of n-butyl lithium in hexane (1.55M; 2 ml.). The mixture was stirred at room temperature for three hours and then evaporated to dryness. The residue was partitioned between EtOAc and water and the EtOAc phase was dried and evaporated to dryness. The residue was recrystallised from EtOH to give 4-[2-(3-t-butylthioureido)pyrid-6-ylthio]butyronitrile (0.32 g.), m.p. 156°-157°.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between EtOAc and water
  3. dry with materialthe EtOAc phase was dried
  4. customevaporated to dryness
  5. customThe residue was recrystallised from EtOH

Sources & evidence

ORD record
ord-a7b33511a3df4da28c8c0a7c674e868c
Source dataset
uspto-grants-1987_09
Patent number
US04696933

Reaction notes

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