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

HRID 1654909Notes

Reaction equation

HRID 1654909 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[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>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)=[S:27])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 164804-Chlorophenyl isothiocyanateHCID 100143212-Amino-3-(2,4-difluorobenzyloxy)pyridine

Product 1

HCID 20077041N-(3-(2,4-Difluorobenzyloxy)pyrid-2-yl)-N'-(4-chlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2,4-difluorobenzyloxy)pyridine (2.10 g, 0.009 mol), 4chlorophenyl isothiocyanate (1.81 g, 0.01 mol) and toluene (10 ml) was refluxed for 3.5 hours, then cooled and treated with diethyl ether to induce crystallisation of the product. Yield2.94 g (81%), m.p.154°-156 ° C.

Workup

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

Sources & evidence

ORD record
ord-e927680d1ef2484191217da21631a20c
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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