Toluene → 3-(2,4,6-Trifluorobenzyloxy)pyrid-2-yl-N'-(4-chlorophenyl)thiourea

HRID 1654911Notes

Reaction equation

HRID 1654911 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([F:16])=[CH:14][C:13]([F:17])=[CH:12][C:11]=2[F:18])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[S:28])=[CH:22][CH:21]=1.C1(C)C=CC=CC=1>C(OCC)C>[F:16][C:15]1[CH:14]=[C:13]([F:17])[CH:12]=[C:11]([F:18])[C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:27]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)=[S:28])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 164804-Chlorophenyl isothiocyanateHCID 100151612-Amino-3-(2,4,6-trifluorobenzyloxy)pyridine

Product 1

HCID 200770093-(2,4,6-Trifluorobenzyloxy)pyrid-2-yl-N'-(4-chlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2,4,6-trifluorobenzyloxy)pyridine (2.29 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. Yield 3.03 g (79.5%), m.p.181°-183 ° C.

Workup

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

Sources & evidence

ORD record
ord-2c38946663564af9b9e2c72d913ca0cc
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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