3-Cyanophenyl isothiocyanate → 1-(3-Cyanophenyl)-3-(1,2,2-trimethyl-propyl)-thiourea

HRID 1241615

Reaction equation

HRID 1241615 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[S:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:12][C:13]([CH3:18])([CH3:17])[CH:14]([NH2:16])[CH3:15]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:16][CH:14]([CH3:15])[C:13]([CH3:18])([CH3:17])[CH3:12])=[S:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 765783-Cyanophenyl isothiocyanateHCID 5209072-Butanamine, 3,3-dimethyl-

Product 1

HCID 38203771-(3-Cyanophenyl)-3-(1,2,2-trimethyl-propyl)-thioureaYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-cyanophenyl isothiocyanate (1.00 g, 6.24 mmol) in THF (25 mL) at room temperature was added (±) 3,3-dimethyl-2-aminobutane (1.08 mL, 9.36 mmol) and the reaction was stirred overnight at room temperature. The mixture was concentrated in vacuo and the resulting residue was triturated with diethyl ether and filtered to afford 1.2 g (78%) of 1-(3-cyanophenyl)-3-(1,2,2-trimethyl-propyl)-thiourea as a white solid which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting residue was triturated with diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c10838b872de494bbe742aea4651c8dc
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Linked notes

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