Neopentylamine → N'-(2,2-Dimethylpropyl)-N-pyridin-3-ylcarbamimidothioic acid

HRID 1241630Notes

Reaction equation

HRID 1241630 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]=[C:8]=[S:9])[CH:2]=1.[CH2:10]([NH2:15])[C:11]([CH3:14])([CH3:13])[CH3:12]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([NH:15][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[S:9])[CH:2]=1

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 27372423-Pyridyl isothiocyanate

Product 1

HCID 3042815N'-(2,2-Dimethylpropyl)-N-pyridin-3-ylcarbamimidothioic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-pyridyl-isothiocyanate (1.50 mL, 13.3 mmol) in THF (30 mL) at room temperature was added neopentylamine (2.35 mL, 19.8 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 2.64 g (89%) of 1-(3-pyridyl)-3-(2,2-dimethylpropyl)-thiourea as an off-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-013cdad7b6864a5da935ab3e6ff0ae27
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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