Toluene → N-[3-(2-chloro-6 fluorobenzyloxy)pyrid-2-yl]-N'-(4-nitrophenyl)thiourea

HRID 1654893Notes

Reaction equation

HRID 1654893 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[S:29])=[CH:23][CH:22]=1)([O-:20])=[O:19].C1(C)C=CC=CC=1>CCOCC>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:28]([NH:27][C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:26][CH:25]=2)=[S:29])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 75044Benzene, 1-isothiocyanato-4-nitro-HCID 101062702-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridine

Product 1

HCID 20077035N-[3-(2-chloro-6 fluorobenzyloxy)pyrid-2-yl]-N'-(4-nitrophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-3-(2-chloro-6-fluorobenzyloxy)pyridine (7.01g, 0.028 mol), 4nitrophenyl isothiocyanate (5.31g, 0.03 mol) and toluene (50 ml) was heated under reflux for 2 hours, then cooled and treated with ether to induce crystallisation of the product. Yield 11.07 g (86%), m.p. 214° 215 ° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. customcrystallisation of the product
  5. customYield 11.07 g (86%), m.p. 214° 215 ° C.

Sources & evidence

ORD record
ord-2ae5d1d4d4e447d2b7787f6dfbfa03e2
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

Loading…