Carbon Disulfide → HCID 13671599, compound

HRID 569457Notes

Reaction equation

HRID 569457 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH2:13])(=[O:12])=[O:11].[C:16](=S)=[S:17].[OH-].[K+].C(OCC)(=O)C>CN(C)C=O>[F:15][C:2]([F:1])([F:14])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]=[C:16]=[S:17])(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8857Ethyl AcetateHCID 14797Potassium Hydroxide2×HCID 27772082-(Trifluoromethoxy)benzenesulfonamide

Product 1

HCID 13671599HCID 13671599, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

24.1 g (0.1 mole) of 2-trifluoromethoxy-benzene-sulphonic acid amide are dissolved in 100 ml of dimethylformamide. 7.6 g (0.1 mole) of carbon disulphide and 5.6 g (0.1 mole) of potassium hydroxide powder are added and the reaction mixture is stirred at 35° C. until a clear solution has formed. A further 5.6 g (0.1 mole) of potassium hydroxide powder are then added and stirring is continued until a clear solution is formed. 100 ml of ethyl acetate are then added dropwise at 20° C. The product thereby obtained as crystals is isolated by filtration with suction and dried under reduced pressure. The dried product is suspended in 100 ml of toluene; 20 g of liquid phosgene are added dropwise at 0° C. and the mixture is stirred at 5° C. to 10° C. for one hour and at 20° C. for two hours. After filtration, the filtrate is concentrated to give an oily residue, which essentially contains 2-trifluoromethoxy-phenylsulphonyl isothiocyanate. Because of its low stability, the product is reacted as quickly as possible--without further purification--in the process according to the invention.

Workup

  1. customhas formed
  2. stirringstirring
  3. customis formed
  4. customThe product thereby obtained as crystals
  5. customis isolated by filtration with suction
  6. customdried under reduced pressure
  7. addition20 g of liquid phosgene are added dropwise at 0° C.
  8. stirringthe mixture is stirred at 5° C. to 10° C. for one hour and at 20° C. for two hours
  9. filtrationAfter filtration
  10. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-54f5efabadda408a97642ed5ecb4b0c8
Source dataset
uspto-grants-1988_03
Patent number
US04732711

Reaction notes

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