Toluene → N-[3-(2-Fluoro-6-chlorobenzyloxy)pyrid-2-yl]-N'-(4-chlorophenyl)thiourea

HRID 1654889Notes

Reaction equation

HRID 1654889 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[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]=[CH:13][CH:14]=[C:15]([Cl:16])[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 101062702-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridine

Product 1

HCID 20076944N-[3-(2-Fluoro-6-chlorobenzyloxy)pyrid-2-yl]-N'-(4-chlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2-fluoro-6-chlorobenzyloxy)pyridine (3.46 g, 0.014 mol), 4chlorophenyl isothiocyanate (2.55 g, 0.015 mol) and toluene (10 ml) was refluxed for 2 hours, then cooled and treated with diethyl ether to induce crystallisation of the product. Yield 4.64 g (73%), m.p. 162°-164 ° C.

Workup

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

Sources & evidence

ORD record
ord-b1400e38b4844ad18d934f23a92c4b89
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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