Hydrochloric Acid → HCID 14305467, compound

HRID 1607683Notes

Reaction equation

HRID 1607683 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20][N:21]([CH3:26])[S:22](Cl)(=[O:24])=[O:23].Cl>N1C=CC=CC=1>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[O:11][C:3]1[CH:4]=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[NH:1][S:22](=[O:24])(=[O:23])[N:21]([CH3:26])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 83372Dimethylsulphamoyl chlorideHCID 10061288HCID 10061288, compound

Product 1

HCID 14305467HCID 14305467, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4'-amino-3'-(2,4-difluorophenoxy)acetophenone (2.0 g) and dimethylsulfamoyl chloride (11 g) in pyridine (20 ml) was stirred for 11 hours at 80° C. After cooling, the reaction mixture was poured into 2N aqueous solution of hydrochloric acid (200 ml) and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (100 g) eluting with a mixture of toluene and ethyl acetate (20:1), and recrystallized from a mixture of ethanol and water (2:1, 15 ml) to give prisms of 3'-(2,4-difluorophenoxy)-4'-(dimethylsulfamoylamino)acetophenone (0.94 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (100 g)
  7. washeluting with a mixture of toluene and ethyl acetate (20:1)
  8. customrecrystallized from a mixture of ethanol and water (2:1, 15 ml)

Sources & evidence

ORD record
ord-3bd93a82819c425bbce2dd6c58ec38fa
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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