Thiophosgene → 4-Isopropoxy-3-isothiocyanato-benzenesulfonamide

HRID 333586Notes

Reaction equation

HRID 333586 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:8]=[C:9]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15].[C:21](Cl)(Cl)=[S:22]>O.C(Cl)(Cl)Cl>[CH:14]([O:13][C:12]1[CH:11]=[CH:10][C:9]([S:17]([NH2:20])(=[O:18])=[O:19])=[CH:8][C:7]=1[N:6]=[C:21]=[S:22])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 696691073-Amino-4-isopropoxy-benzenesulfonamide

Product 1

HCID 866653704-Isopropoxy-3-isothiocyanato-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of sodium bicarbonate (16.8 g, 199.5 mmol) in water (400 mL) was added to 3-amino-4-isopropoxy-benzenesulfonamide (15.3 g, 66.5 mmol, example 2, step d) in a mixture of chloroform (200 mL) and water (200 mL). Thiophosgene (6.37 mL, 83.1 mmol) was then added. The biphasic solution was stirred at room temperature for 1.5 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was washed with water, dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as a tan solid.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc165a36b5d44f3492a4ade0d8299700
Source dataset
uspto-grants-2014_11
Patent number
US08883473B2

Reaction notes

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