HCID 70376886, compound → HCID 10655069, compound

HRID 358703Notes

Reaction equation

HRID 358703 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9]S(C)=O)=[C:4]([NH:14][CH3:15])[CH:3]=1>C(O)(=O)C.C(O)C.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH3:9])=[C:4]([NH:14][CH3:15])[CH:3]=1

Participants

5

Reactant 1

HCID 70376886HCID 70376886, compound

Product 1

HCID 10655069HCID 10655069, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Procedure

A solution of 1-[4-chloro-2-(methylamino)phenyl-2-methylsulphinylethanone (17 g) in a mixture of glacial acetic acid (35 ml) and absolute ethanol (35 ml) was added dropwise over 20 minutes to a stirred suspension of zinc dust (22.5 g) in acetic acid (20 ml) and absolute ethanol (35 ml) under nitrogen at ambient temperature. After stirring at ambient temperature for 24 hours, the reaction mixture was filtered through diatomaceous earth (sold under the trade name CELITE) and the filter bed was washed with glacial acetic acid (200 ml). Water (600 ml) was added to the combined filtrate and washing and the mixture was extracted with dichloromethane (3×200 ml). The combined extracts were dried over magnesium sulphate and the solvent was removed by distillation to give the novel compound 4'-chloro-2'-(methylamino)acetophenone, m.p. 65°-66°.

Workup

  1. filtrationthe reaction mixture was filtered through diatomaceous earth (
  2. washwas washed with glacial acetic acid (200 ml)
  3. additionWater (600 ml) was added to the combined filtrate
  4. washwashing
  5. extractionthe mixture was extracted with dichloromethane (3×200 ml)
  6. dry with materialThe combined extracts were dried over magnesium sulphate
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-6cd77571718a4e15a80bae8a2803d6a5
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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