Toluene → N-(3-(4-Methoxybenzyloxy)pyrid-2-yl)-N'-(4-chlorophenyl)thiourea

HRID 1654882Notes

Reaction equation

HRID 1654882 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1.C1(C)C=CC=CC=1>C(OCC)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:7]2[C:2]([NH:1][C:26]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=3)=[S:27])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 164804-Chlorophenyl isothiocyanateHCID 27283893-[(4-Methoxybenzyl)oxy]pyridin-2-amine

Product 1

HCID 20076976N-(3-(4-Methoxybenzyloxy)pyrid-2-yl)-N'-(4-chlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(4-methoxybenzyloxy)pyridine (1.80 g, 0.0078 mol), 4chlorophenyl isothiocyanate (1.58 g, 0.0094 mol) and toluene (10 ml) was refluxed for 3.5 hours, then cooled and treated with diethyl ether to induce crystallisation of the product. Yield 2.2 g (70.5%), m.p. 136°-138 ° C.

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. temperaturecooled
  3. customcrystallisation of the product

Sources & evidence

ORD record
ord-1db6ed41fc37437e83c0fec0424c0677
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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