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

HRID 1654891Notes

Reaction equation

HRID 1654891 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.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]=[C:26]=[S:27].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:26]([NH:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[F:18])=[S:27])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 975202-Fluorophenyl isothiocyanateHCID 101062702-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridine

Product 1

HCID 20076947N-[3-(2-Chloro-6-fluorobenzyloxy)pyrid-2-yl]-N'-(2-fluorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2-chloro-6-fluorobenzyloxy)pyridine (7.48g, 0.03 mol), 2fluorophenyl isothiocyanate (5.0 g, 0.033 mol) and toluene (30 ml) was heated under reflux for 1.5 hours, then cooled and diluted with ether to induce crystallisation of the product. Yield 7.9 g (59 %), m.p. 145°-147 ° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled
  4. customcrystallisation of the product

Sources & evidence

ORD record
ord-761b22b4275b429f839604821279b0a2
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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