1,3-Dichloro-2-isothiocyanatobenzene → N-(2-Amino-5-fluorophenyl)-N′-(2,6-dichlorophenyl)thiourea

HRID 2119574Notes

Reaction equation

HRID 2119574 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[N:18]=[C:19]=[S:20]>CC(=O)OCC>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:9][C:19]([NH:18][C:12]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:11]=1[Cl:10])=[S:20]

Participants

4

Reactant 2

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 1645844-Fluorobenzene-1,2-diamine

Product 1

HCID 22288818N-(2-Amino-5-fluorophenyl)-N′-(2,6-dichlorophenyl)thioureaYield 77.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.37 g (0.0346 mol) of 4-fluoro-1,2-diaminobenzene and 7.07 g (0.0346 mol) of 2,6-dichlorophenyl isothiocyanate in 150 ml of EA was boiled under reflux for 3 hours. After distilling off the solvent, the residue was dissolved in methanol, treated with activated carbon, ⅔ of the solvent volume was distilled off, and the thiourea was allowed to crystallize in an ice bath for a number of hours. 8.9 g of the desired product was obtained. Colorless crystals, 1st m.p.: 175-178° C.; 2nd m.p.: 294-296° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationAfter distilling off the solvent
  3. dissolutionthe residue was dissolved in methanol
  4. additiontreated with activated carbon, ⅔ of the solvent volume
  5. distillationwas distilled off
  6. customto crystallize in an ice bath for a number of hours

Sources & evidence

ORD record
ord-1a6998b35fe34e99add7622434af7af1
Source dataset
uspto-grants-2004_02
Patent number
US06686384B2

Reaction notes

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