tert-Butyl isothiocyanate → HCID 54198371, compound

HRID 2413145Notes

Reaction equation

HRID 2413145 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-37ba3ca65ae840308e004b2f19e4961e
Source dataset
uspto-grants-1985_01
Patent number
US04496564

Reaction notes

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