Toluene → N-[3-(2-Chloro-6-fluorobenzyloxy)pyrid-2-yl]-N'-(2-methyl-4chlorophenyl)thiourea

HRID 1654899

Reaction equation

HRID 1654899 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[N:26]=[C:27]=[S:28].C1(C)C=CC=CC=1>CCOCC>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:27]([NH:26][C:20]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=2[CH3:18])=[S:28])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 900213-Chloro-6-isothiocyanatotolueneHCID 101062702-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridine

Product 1

HCID 20076993N-[3-(2-Chloro-6-fluorobenzyloxy)pyrid-2-yl]-N'-(2-methyl-4chlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2-chloro-6-fluorobenzyloxy)pyridine (2 g, 0.008 mol), (2-methyl-4-chlorophenyl isothiocyanate (1.76 g, 0.0096 mol) and toluene (10 ml) was heated under reflux for 5 hours, then cooled and diluted with ether to induce crystallisation of the product. Yield 2.72g (77%), m.p. 176°-177 ° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperaturecooled
  3. customcrystallisation of the product

Sources & evidence

ORD record
ord-0d0639210ed94f608b1871b9a829d93e
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Linked notes

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