Chlorosulfonic acid → (R)-N-[4-Chlorosulphonyl-3-iodo-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2120359Notes

Reaction equation

HRID 2120359 reaction equation
[I:1][C:2]1[C:3]([Cl:18])=[C:4]([NH:8][C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:6][CH:7]=1.[Cl:19][S:20](O)(=[O:22])=[O:21]>>[Cl:19][S:20]([C:7]1[CH:6]=[CH:5][C:4]([NH:8][C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12])=[C:3]([Cl:18])[C:2]=1[I:1])(=[O:22])=[O:21]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 69539506(R)-N-[3-Iodo-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Product 1

HCID 86759333(R)-N-[4-Chlorosulphonyl-3-iodo-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Conditions

Temperature
80 °C

Procedure

(R)-N-[3-Iodo-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 31) (4.92 g) was added in portions to chlorosulphonic acid (18 ml) at 0° C. The reaction mixture was heated to 80° C. for 4 hours, allowed to cool to ambient temperature and poured onto ice-water (200 g). The mixture was extracted into DCM (2×250 ml), the organic phase was washed with brine (300 ml) and dried. Volatile material was removed by evaporation to give the title compound (4.8 g) as a brown gum. NMR (CDCl3) 1.78 (s, 3H), 3.59 (s, 1H), 8.23 (d, 1H), 8.74 (d, 1H), 9.53 (s, 1H); m/z: 490.

Workup

  1. temperatureto cool to ambient temperature
  2. additionpoured onto ice-water (200 g)
  3. extractionThe mixture was extracted into DCM (2×250 ml)
  4. washthe organic phase was washed with brine (300 ml)
  5. customdried
  6. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-6dab1be9818c4f859a8d57c9b94adef7
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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