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Thionyl Chloride → N-Cyano-N'-methyl-N"-[2-(2-(2-pyrimidyl)ethyl)thioethyl]guanidine

HRID 1577200
Notes
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Reaction equation

HRID 1577200 reaction equation
ClCCC1N=CC=CN=1.OCCN1C=CC=NC1.S(Cl)(Cl)=O.[NH2:23][CH2:24][CH2:25][S:26][CH2:27][CH2:28][C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1.[C:35]([NH:37][C:38](=[N:41][CH3:42])SC)#[N:36]>>[C:35]([NH:37][C:38]([NH:41][CH3:42])=[N:23][CH2:24][CH2:25][S:26][CH2:27][CH2:28][C:29]1[N:30]=[CH:31][CH:32]=[CH:33][N:34]=1)#[N:36]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 24386Thionyl ChlorideHCID 1111031-Cyano-2,3-dimethylisothioureaHCID 205675002-(2-Chloroethyl)pyrimidineHCID 205677192-[2-(2-Aminoethyl)thioethyl]pyrimidineHCID 205718123-(2-Hydroxyethyl)pyrimidine

Product 1

HCID 178485017N-Cyano-N'-methyl-N"-[2-(2-(2-pyrimidyl)ethyl)thioethyl]guanidine

Procedure

By the procedure of Example 17 using 2-(2-chloroethyl)pyrimidine, prepared by treating 3-(2-hydroxyethyl)pyrimidine with thionyl chloride, as the starting material, 2-[2-(2-aminoethyl)thioethyl]pyrimidine is prepared, which when treated with N-cyano-N',S-dimethylisothiourea by the procedure of Example 3(a) gives the title compound.

Sources & evidence

ORD record
ord-66674cf190864acf9fc3d77601b3b589
Source dataset
uspto-grants-1981_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04287198

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes