Chlorosulfonyl isocyanate → HCID 19813655, compound

HRID 467227Notes

Reaction equation

HRID 467227 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[CH3:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])[N:10]=1>C(OCC)(=O)C>[CH3:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[N:12]=[C:11]([N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:27])([F:29])[F:28])[C:6]([NH2:5])=[O:7])[N:10]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 19813653HCID 19813653, compound

Product 1

HCID 19813655HCID 19813655, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
3 °C

Procedure

At 3° C., 3.6 g (0.026 mole) of chlorosulfonyl isocyanate are added to a solution of 6.4 g (0.02 mole) of N-(4-methyl-6-trifluoromethyl-pyrimidin-2-yl)-2-trifluoromethylaniline in 100 ml of ethyl acetate. After stirring the batch for 2 hours at 3° C., 100 ml of ethyl acetate and 50 ml of ice-water are added. The aqueous phase is separated off, and the organic phase is washed with sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in a rotary evaporator. The crystals remaining are triturated with hexane, filtered off and dried in vacuo at 40° C. 6.1 g (83.8%) of the title compound of formula ##STR11## are isolated in the form of crystals having a melting point of 150°-153° C. (Comp. No. 1.020).

Workup

  1. customThe aqueous phase is separated off
  2. washthe organic phase is washed with sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation in a rotary evaporator
  5. customThe crystals remaining are triturated with hexane
  6. filtrationfiltered off
  7. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-c20054233f684d369c688c8e060c803b
Source dataset
uspto-grants-1992_10
Patent number
US05159078

Reaction notes

Loading…