Toluene → N-[3-(4-Methoxybenzyloxy)pyrid-2-yl]-N'-phenylthiourea

HRID 1654880Notes

Reaction equation

HRID 1654880 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[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>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:7]2[C:2]([NH:1][C:25]([NH:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[S:26])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7673Phenyl IsothiocyanateHCID 27283893-[(4-Methoxybenzyl)oxy]pyridin-2-amine

Product 1

HCID 20076982N-[3-(4-Methoxybenzyloxy)pyrid-2-yl]-N'-phenylthiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(4-methoxybenzyloxy)pyridine (1.91 g, 0.0083 mol), phenyl isothiocyanate (1.4 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 2.18 g (72%), m.p. 123°-125 ° C.

Workup

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

Sources & evidence

ORD record
ord-a2681fa8ea7a4ddeb3f2ce3dfa836485
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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