Thiophosgene → 1-{[3-(1,1-Dimethylethyl)phenyl]oxy}-4-isothiocyanato-2,5-dimethylbenzene

HRID 2121834Notes

Reaction equation

HRID 2121834 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][C:6]([C:9]1[CH:10]=[C:11]([O:15][C:16]2[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:8][C:6]([C:9]1[CH:10]=[C:11]([O:15][C:16]2[CH:17]=[C:18]([CH3:24])[C:19]([N:20]=[C:1]=[S:2])=[CH:21][C:22]=2[CH3:23])[CH:12]=[CH:13][CH:14]=1)([CH3:5])[CH3:7]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 155445904-((3-(1,1-Dimethyl-ethyl)phenyl)oxy)-2,5-dimethylaniline

Product 1

HCID 234343591-{[3-(1,1-Dimethylethyl)phenyl]oxy}-4-isothiocyanato-2,5-dimethylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Thiophosgene (0.38 ml) is added to a two-phase mixture at room temperature of 4-((3-(1,1-dimethyl-ethyl)phenyl)oxy)-2,5-dimethylaniline (1.35 g) in toluene (6 ml) and sodium bicarbonate (840 mg) in water (6 ml). The reaction mixture obtained is stirred for 2 h and the phases are then separated by settling. The aqueous phase is extracted with toluene and the combined organic phases are then washed with water, dried (magnesium sulphate) and then concentrated to give the title product.

Workup

  1. customThe reaction mixture obtained
  2. customthe phases are then separated
  3. extractionThe aqueous phase is extracted with toluene
  4. washthe combined organic phases are then washed with water
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d6cbb2c7c40474b95fa020414f74a29
Source dataset
uspto-grants-2004_02
Patent number
US06696487B2

Reaction notes

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