Thiophosgene → 4-(2,5-Dichloro-phenoxy)-3-fluoro-phenylisothiocyanate

HRID 33760

Reaction equation

HRID 33760 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[F:12].C(=O)(O)[O-].[Na+].[C:23](Cl)(Cl)=[S:24]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:23]=[S:24])=[CH:7][C:6]=1[F:12]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 289727064-(2,5-Dichlorophenoxy)-3-fluoroaniline

Product 1

HCID 597976634-(2,5-Dichloro-phenoxy)-3-fluoro-phenylisothiocyanateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4-(2,5-Dichloro-phenoxy)-3-fluoro-phenylamine (1.36 g, 5 mmol) was dissolved in 150 ml of chloroform and 100 ml of saturated aqueous sodium bicarbonate was added. To this biphasic mixture was added dropwise a solution of thiophosgene (0.39 ml, 5 mmol) in 30 ml of chloroform at room temperature with vigorous stirring. The mixture was stirred vigorously for 1 hour at room temperature. The bottom layer of the mixture was separated, and the aqueous layer was extracted twice with CHCl3. The combined organic solution was washed with water, dried over Mg2SO4 and evaporated to give 1.53 g (97.4%) of crude product used for next step without further purification.

Workup

  1. customThe bottom layer of the mixture was separated
  2. extractionthe aqueous layer was extracted twice with CHCl3
  3. washThe combined organic solution was washed with water
  4. dry with materialdried over Mg2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b997bf5941b9465ca8966a1a87240e14
Source dataset
uspto-grants-2008_09
Patent number
US07429667B2

Linked notes

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