Methyl isothiocyanate → N-methyl-N'-ethyl-N'-(3-pyridylmethyl)thiourea

HRID 1682224Notes

Reaction equation

HRID 1682224 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[CH3:2].[CH3:11][N:12]=[C:13]=[S:14]>C(OCC)C>[CH3:11][NH:12][C:13]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[S:14]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 4716480Ethyl[(pyridin-3-yl)methyl]amine

Product 1

HCID 22450434N-methyl-N'-ethyl-N'-(3-pyridylmethyl)thioureaYield 100.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

In 50 ml of ethyl ether was dissolved 2.4 g of N-ethyl-N-(3-pyridylmethyl)amine followed by addition of 1.3 g of methyl isothiocyanate. The mixture was stirred at room temperature (25° C.) for 1 hour. The resulting precipitate was collected by filtration, washed with a small amount of ethyl ether and dried to give 3.7 g of N-methyl-N'-ethyl-N'-(3-pyridylmethyl)thiourea as white prisms.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with a small amount of ethyl ether
  3. customdried

Sources & evidence

ORD record
ord-fa15ae349e644721bf22c9c3ab55c84d
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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