Toluene → N-[3-(2-Methylbenzyloxy)pyrid-2-yl]-N'-(4-chlorophenyl)thiourea

HRID 1654872Notes

Reaction equation

HRID 1654872 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[S:26])=[CH:20][CH:19]=1.C1(C)C=CC=CC=1>CCOCC>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)=[S:26])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 164804-Chlorophenyl isothiocyanateHCID 138258823-[(2-Methylphenyl)methoxy]pyridin-2-amine

Product 1

HCID 20077040N-[3-(2-Methylbenzyloxy)pyrid-2-yl]-N'-(4-chlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2-methylbenzyloxy)pyridine (1.19 g, 0.0056 mol), 4-chlorophenyl isothiocyanate (1.15 g, 0.0068 mol) and toluene (10 ml) was refluxed for 2.5 hours, then cooled and treated with ether to induce crystallisation of the product. Yield 1.63 g (77%), m.p. 181°-183 ° C.

Workup

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

Sources & evidence

ORD record
ord-cf3a877fdba34dfdb85e92becbb0ed01
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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