HCID 67930067, compound → HCID 67930059, compound

HRID 358709Notes

Reaction equation

HRID 358709 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9](=[O:14])[CH2:10]S(C)=O)=[C:4]([NH:15][CH3:16])[CH:3]=1>C(O)(=O)C.C(O)C.[Zn]>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9](=[O:14])[CH3:10])=[C:4]([NH:15][CH3:16])[CH:3]=1

Participants

5

Reactant 1

HCID 67930067HCID 67930067, compound

Product 1

HCID 67930059HCID 67930059, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Procedure

A solution of 1-[4,5-difluoro-2-(methylamino)phenyl]-2-methylsulphinylethanone (32.4 g) in acetic acid (90 ml) and ethanol (90 ml) was added over a period of 20 minutes to a stirred suspension of zinc dust (50 g) in acetic acid (45 ml) and ethanol (80 ml) at 0° under nitrogen. The mixture was stirred at ambient temperature overnight and then filtered through diatomaceous earth (sold under the trade name CELITE). The filter bed was washed with acetic acid (3×50 ml). The combined filtrate and washings were poured into water (1200 ml) and the mixture was extracted with dichloromethane (3×400 ml). The combined extracts were washed with aqueous sodium carbonate (1M, 2×500 ml) and dried over magnesium sulphate. The solvent was removed by distillation to give the novel compound 4',5'-difluoro-2'-(methylamino)acetophenone, m.p 51°-52°.

Workup

  1. filtrationfiltered through diatomaceous earth (
  2. washThe filter bed was washed with acetic acid (3×50 ml)
  3. additionThe combined filtrate and washings were poured into water (1200 ml)
  4. extractionthe mixture was extracted with dichloromethane (3×400 ml)
  5. washThe combined extracts were washed with aqueous sodium carbonate (1M, 2×500 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-ad597898248f4973b53d32c398666e6b
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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