Dichloromethane → HCID 22611262, compound

HRID 975151Notes

Reaction equation

HRID 975151 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[CH3:3].ClCCl>[O-2].[O-2].[Mn+4].C(#N)C>[C:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)(=[O:1])[CH3:3]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 19970922HCID 19970922, compound

Product 1

HCID 22611262HCID 22611262, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of the title compound of Example 56 (160 mg, 0.62 mmol), activated manganese dioxide (1.6 g), dichloromethane (12 ml) and acetonitrile (3 ml) was stirred for 16 hours at room temperature, when a further portion of activated manganese dioxide (0.6 g) was added. After a further 4 days, the reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with 0.880 aqueous ammonia:methanol:dichloromethane (1:12:5:86.5), to afford the title compound (35 mg). Rf 0.35 (SS 15). Found: C,73.30; H,7.76; N,10.65. C16H20N2O; 0.17 CH2Cl2 requires C,73.73; H,7.75; N,10.71%.

Workup

  1. waitAfter a further 4 days
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with 0.880 aqueous ammonia:methanol:dichloromethane (1:12:5:86.5)

Sources & evidence

ORD record
ord-5ccece5aa2f147498d14cd6453175d83
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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