1,3-Dichloro-2-isothiocyanatobenzene → 1-(2-Amino-3,4,5,6-tetrafluorophenyl)-3-(2,6-dichloro-phenyl)thiourea

HRID 2119579Notes

Reaction equation

HRID 2119579 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[NH2:12].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[N:21]=[C:22]=[S:23]>C1COCC1>[NH2:12][C:3]1[C:4]([F:11])=[C:5]([F:10])[C:6]([F:9])=[C:7]([F:8])[C:2]=1[NH:1][C:22]([NH:21][C:15]1[C:16]([Cl:20])=[CH:17][CH:18]=[CH:19][C:14]=1[Cl:13])=[S:23]

Participants

4

Reactant 2

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 27739573,4,5,6-Tetrafluorobenzene-1,2-diamine

Product 1

HCID 222888221-(2-Amino-3,4,5,6-tetrafluorophenyl)-3-(2,6-dichloro-phenyl)thioureaYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Amino-3,4,5,6-tetrafluorophenyl)-3-(2,6-dichlorophenyl)thiourea was obtained by boiling a mixture of 1 g of 1,2-diamino-3,4,5,6-tetrafluorobenzene with 1.13 g of 2,6-dichlorophenyl isothiocyanate in 30 ml of anhydrous THF for 4 hours. After distilling off the solvent, the thiourea was brought to crystallization under diisopropyl ether and 1.88 g of 1-(2-amino-3,4,5,6-tetrafluorophenyl)-3-(2,6-dichloro-phenyl)thiourea were obtained as a crystalline solid. M.p.: >300° C.

Workup

  1. distillationAfter distilling off the solvent
  2. customthe thiourea was brought to crystallization under diisopropyl ether

Sources & evidence

ORD record
ord-025cdafe5ae24ec6b7c0badfebfeb8c3
Source dataset
uspto-grants-2004_02
Patent number
US06686384B2

Reaction notes

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