Methyl isothiocyanate → N-methyl-N'-[2-((4-chloro-2-methyl-5-pyrimidyl)methylthio)ethyl]thiourea

HRID 904382Notes

Reaction equation

[H-].[Na+].C[N:4]=[C:5]=S.[Cl:7]CC1N=CC=CN=1.C1(=O)[N:19]([CH2:20][CH2:21][CH2:22][SH:23])[C:18](=O)[C:17]2=CC=CC=C12.[CH3:30][NH:31][C:32]([NH:34][CH2:35][CH2:36]CSCC1N=CC=CN=1)=[S:33]>>[CH3:30][NH:31][C:32]([NH:34][CH2:35][CH2:36][S:23][CH2:22][C:21]1[C:5]([Cl:7])=[N:4][C:18]([CH3:17])=[N:19][CH:20]=1)=[S:33]

Participants

Reactant 5

HCID 11167Methyl isothiocyanate

HCID 24758Sodium hydride

HCID 110204412-(3-Mercaptopropyl)isoindoline-1,3-dione

HCID 128773712-(Chloromethyl)pyrimidine

HCID 20557895N-methyl-N'-[3-(2-pyrimidylmethylthio)propyl]thiourea

Product 1

HCID 20557890N-methyl-N'-[2-((4-chloro-2-methyl-5-pyrimidyl)methylthio)ethyl]thiourea

Procedure

In the procedure of Example 1(i) (b) and (ii), using 2-chloromethylpyrimidine and 3-phthalimidopropanethiol as the starting materials, the product is N-methyl-N'-[3-(2-pyrimidylmethylthio)propyl]thiourea.

Sources & evidence

ORD record: ord-69acbada7fb246f98b947985350b415d
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230865

Reaction notes

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