Methanol → HCID 21162409, compound

HRID 894008Notes

Reaction equation

HRID 894008 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])=[CH:17][C:11]=3[C:10](=[O:23])[CH2:9][C:8]=2[CH:24]=1)([O-:3])=[O:2].CO.[C:27](=O)([O-])O.[Na+]>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([CH:18]([CH3:22])[C:19]([O:21][CH3:27])=[O:20])=[CH:17][C:11]=3[C:10](=[O:23])[CH2:9][C:8]=2[CH:24]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 12895879HCID 12895879, compound

Product 1

HCID 21162409HCID 21162409, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 72 mg of 2-(10,11-dihydro-8-nitro-11-oxodibenzo[b,f]-thiepin-2-yl)-propionic acid were added 10 ml of a diazomethaneether solution and 1 ml of methanol, and the mixture was stirred at room temperature for 30 minutes. To this was added acetic acid, and the mixture was made alkaline with a saturated sodium hydrogen carbonate solution and then extracted with benzene. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain a yellow oil, which was chromatographed over 2 g of silica gel and eluted with chloroform, thereby obtaining 44 mg (yield: 57%) of methyl 2-(10,11-dihydro-8-nitro-11-oxodibenzo[b,f]thiepin-2-yl)-propionate as a yellow oil.

Workup

  1. extractionextracted with benzene
  2. washThe extract was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation
  5. customto obtain a yellow oil, which
  6. customwas chromatographed over 2 g of silica gel
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-ef3417ba6d4244f68c78f835bf47bd61
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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