Dichloromethane → 1-(6-Chloro-3-pyridylmethyl)-1,3-dimethylthiourea

HRID 1091062Notes

Reaction equation

HRID 1091062 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].ClC1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][CH3:14])=[CH:8][N:7]=1.Cl[CH2:16][Cl:17]>>[Cl:17][C:16]1[N:7]=[CH:8][C:9]([CH2:12][N:13]([CH3:14])[C:3]([NH:2][CH3:1])=[S:4])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 11167Methyl isothiocyanateHCID 110948836-Chloro-N-methyl-3-pyridinemethanamine

Product 1

HCID 150289211-(6-Chloro-3-pyridylmethyl)-1,3-dimethylthiourea

Procedure

On a water bath at about 20° C., a solution of 1.44 g of methyl isothiocyanate in 2 ml of dichloromethane was added dropwise to a mixture of 2.81 g of 2-chloro-5-(methylaminomethyl)pyridine and 10 ml of dichloromethane over a period of 10 minutes and the whole mixture was further stirred for 30 minutes. The reaction mixture was then concentrated and the residue was purified by column chromatography (eluent: dichloromethane-methanol (20:1)) to give 3.33 g of 1-(6-chloro-3-pyridylmethyl)-1,3-dimethylthiourea.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by column chromatography (eluent: dichloromethane-methanol (20:1))

Sources & evidence

ORD record
ord-1bbe108b81134f81ba90b3ea44db82ec
Source dataset
uspto-grants-1992_01
Patent number
US05084459

Reaction notes

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