Toluene → N-[3-(2,6-Dichlorobenzyloxy)pyrid-2-yl]-N'-phenylthiourea

HRID 1654900Notes

Reaction equation

HRID 1654900 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[Cl: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>CCOCC>[Cl: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 103783682-Amino-3-(2,6-dichlorobenzyloxy)pyridine

Product 1

HCID 20077038N-[3-(2,6-Dichlorobenzyloxy)pyrid-2-yl]-N'-phenylthiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2,6-dichlorobenzyloxy)pyridine (2 g, 0.007 1 mol), phenyl isothiocyanate (1.15 g, 0.0085 mol) and toluene (10 ml) was heated under reflux for 1.5 hours, then cooled and diluted with ether to induce crystallisation of the product, which was recrystallised from ethanol/ether. Yield 1.2 g (42%), m.p. 148°-149 ° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled
  4. customcrystallisation of the product, which
  5. customwas recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-5f09faafa2474b88b46743c60e3dc555
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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