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Methylamine → N-(3,5-Dichloropyridin-2-yl)-N'-methylthiourea

HRID 27902
Notes
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Reaction equation

HRID 27902 reaction equation
[Cl:1][C:2]1[C:3]([N:9]=[C:10]=[S:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:12][NH2:13]>C1C=CC=CC=1.C(O)C>[Cl:1][C:2]1[C:3]([NH:9][C:10]([NH:13][CH3:12])=[S:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6329MethylamineHCID 233404453,5-Dichloro-2-isothiocyanatopyridine

Product 1

HCID 23340446N-(3,5-Dichloropyridin-2-yl)-N'-methylthiourea

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A solution of 3,5 dichloro-2-pyridylisothiocyanate (5.13 g.) in benzene (20 ml.) was added to a solution of methylamine in ethanol (5 ml., 33%) and the mixture was stirred for 18 hours at ambient temperature. Petroleum ether (60°-80° C., 30 ml.) was added and the resulting precipitate was filtered off and recrystallised from benzene-light petroleum to give colourless microcrystals of 1-(3,5-dichloro-2-pyridyl)-3-methyl-2-thiourea (4.18 g.) m.pt. 105°-109° C.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. customrecrystallised from benzene-light petroleum

Sources & evidence

ORD record
ord-447b26ef6ea94b23ada5e0d8ac45c4d5
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04224331

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes