Methyl isothiocyanate → N-methyl-N'-(4-(2-pyridyl)butyl)thiourea

HRID 1076127Notes

Reaction equation

HRID 1076127 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[CH3:12][N:13]=[C:14]=[S:15]>C(O)C>[CH3:12][NH:13][C:14]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[S:15]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 135110834-(Pyridin-2-yl)butan-1-amine

Product 1

HCID 20466716N-methyl-N'-(4-(2-pyridyl)butyl)thioureaYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction of 2-(4-aminobutyl)pyridine (3.0 g) and methyl isothiocyanate (1.6g) in ethanol (25 ml) for 0.5 hours followed by chromatography of the product on silica and elution with ethyl acetate affords N-methyl-N'-(4-(2-pyridyl)butyl)thiourea (3.0 g) as a colourless oil.

Workup

  1. washfollowed by chromatography of the product on silica and elution with ethyl acetate

Sources & evidence

ORD record
ord-877e2e5f4dc947ddbd47e165f5fa26bc
Source dataset
uspto-grants-1976_05
Patent number
US03954982

Reaction notes

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