Toluene → N-[3-(3-chloro-2-fluorobenzyloxy)pyrid-2-yl]-N'-4-chlorophenylthiourea

HRID 1654920Notes

Reaction equation

HRID 1654920 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[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>[Cl:16][C:12]1[C:11]([F:17])=[C:10]([CH:15]=[CH:14][CH:13]=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 103999912-Amino-3-(3-chloro-2-fluorobenzyloxy)pyridine

Product 1

HCID 20077003N-[3-(3-chloro-2-fluorobenzyloxy)pyrid-2-yl]-N'-4-chlorophenylthiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(3-chloro-2-fluorobenzyloxy)pyridine (2.00 g, 0.0079 mol), 4chlorophenyl isothiocyanate (1.61 g, 0.0095 mol) and toluene (10 ml) was refluxed for 3 hours, then cooled and treated with diethyl ether to induce crystallisation of the product. Yield2.37 g (71%),m.p. 174°-176 ° C.

Workup

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

Sources & evidence

ORD record
ord-d47206c9f3a44cb6b416a5b5269076b4
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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