Methylamine → N-(3-(2,6-Dichlorobenzyloxy)pyrid-2-yl)-N'-methyl-N"-(4-chlorophenyl)guanidine

HRID 1654933Notes

Reaction equation

HRID 1654933 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=S)=[N:8][CH:9]=[CH:10][CH:11]=1.[CH3:28][NH2:29]>>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH:12][C:13]([NH:29][CH3:28])=[N:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 20076936N-[3-(2,6-dichlorobenzyloxy)pyrid-2-yl]-N'-(4-chlorophenyl)thiourea

Product 1

HCID 178484918N-(3-(2,6-Dichlorobenzyloxy)pyrid-2-yl)-N'-methyl-N"-(4-chlorophenyl)guanidine

Procedure

A mixture of N-[3-(2,6-dichlorobenzyloxy)pyrid-2-yl]-N'-(4-chlorophenyl)thiourea (2.0 g, 0.0045 mol), yellow mercuric oxide (1.18 g, 0.0054 mol) and 33% w/w methylamine in methylated spirit (40 ml) was stirred at room temperature for 24 hours. The solvent was removed in vacuo and the black residue was boiled with chloroform and filtered hot. Evaporation of the solvent and recrystallisation from acetonitrile gave the desired product. Yield 1.53 g (78%), m.p. 153°-156 ° C.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered hot
  3. customEvaporation of the solvent and recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-4da485ca7b2d4713b1b2f335c443f208
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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