Thiophosgene → HCID 19025388, compound

HRID 1030980Notes

Reaction equation

HRID 1030980 reaction equation
[C:1](Cl)(Cl)=[S:2].C(=O)([O-])[O-].[K+].[K+].[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([CH3:19])[CH:13]=1>O.C(Cl)(Cl)Cl>[I:11][C:12]1[CH:18]=[CH:17][C:15]([N:16]=[C:1]=[S:2])=[C:14]([CH3:19])[CH:13]=1

Participants

6

Reactant 3

HCID 10040Thiophosgene2×HCID 11430Potassium Carbonate2×HCID 832214-Iodo-o-toluidine

Product 1

HCID 19025388HCID 19025388, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 9.9 g (0.086 mole) of thiophosgene, 5.0 g (0.036 mole) of potassium carbonate in 55 ml of water and 100 ml of chloroform was added a solution of 20.0 g (0.0862 mole) of 4-iodo-2-methylaniline in 50 ml of chloroform. Additional potassium carbonate was added to make the reaction mixture basic. An additional 9.9 g of thiophosgene was added, and the reaction mixture was stirred at room temperature for approximately 18 hours. The mixture was partitioned between water (100 ml) and chloroform (100 ml). The organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure, leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride to yield 22.6 g of 4-iodo-2-methylphenyl isothiocyanate as a solid, mp 51°-53° C.

Workup

  1. customThe mixture was partitioned between water (100 ml) and chloroform (100 ml)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationwas filtered
  4. customThe filtrate was evaporated under reduced pressure
  5. customleaving a residue
  6. customThis residue was purified by column chromatography on silica gel
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-88e7d7128c764943a4281e4a272eb740
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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