Methanol → HCID 53910911, compound

HRID 1655494Notes

Reaction equation

HRID 1655494 reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](=[O:20])[C:14](=[N+:18]=[N-:19])[C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:21][OH:22].C(Cl)(Cl)Cl.O>C(N(CC)CC)C>[N+:18](=[C:14]([C:15](=[O:17])[CH3:16])[C:13](=[O:20])[CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([O:22][CH3:21])(=[O:4])=[O:3])=[CH:6][CH:7]=1)=[N-:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6212ChloroformHCID 53743745HCID 53743745, compound2×

Product 1

HCID 53910911HCID 53910911, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

6-(4-Chlorosulfonylphenyl)-3-diazo-2,4-hexanedione (2.0 g, 6.4 mmol) obtained in Example 3, (3) was stirred in triethylamine (1.5 ml), methanol (2.5 ml) and chloroform (8 ml) for 6 h at 10°-15° C., then the mixture was poured into H2O and extracted thrice with chloroform. The organic extract was washed with H2O, dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was chromatographed on silica gel (Wako Gel C-200, manufactured by Wako Pure Chemical Industries, Ltd.) with chloroform as eluent to give the title compound as a pale yellow viscous oil; yield: 730 mg.

Workup

  1. extractionextracted thrice with chloroform
  2. extractionThe organic extract
  3. washwas washed with H2O
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on silica gel (Wako Gel C-200, manufactured by Wako Pure Chemical Industries, Ltd.) with chloroform as eluent

Sources & evidence

ORD record
ord-e948faf1688c4c49a6138ce72b53b477
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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