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

HRID 1654887Notes

Reaction equation

HRID 1654887 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.[C:18]1([N:24]=[C:25]=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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:25]([NH:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[S:26])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7673Phenyl IsothiocyanateHCID 101062702-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridine

Product 1

HCID 20077023N-[3-(2-Fluoro-6-chlorobenzyloxy)pyrid-2-yl]-N'-phenylthiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2-fluoro-6-chlorobenzyloxy)pyridine (7.6 g, 0.03 mol), phenyl isothiocyanate (3.95 ml, 0.033 mol) and toluene (25 ml) was refluxed for 2.5 hours, then cooled and treated with diethyl ether to induce crystallisation of the product. Yield 8.47 g (73%), m.p. 143°-145 ° C.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. temperaturecooled
  3. customcrystallisation of the product

Sources & evidence

ORD record
ord-4416825623b449e1b1d9a0b01589dfe6
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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