Acetic Anhydride → HCID 12043500, compound

HRID 1936868Notes

Reaction equation

HRID 1936868 reaction equation
[N:1]([CH:4]1[CH2:21][CH2:20][C:7]2=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:9][C:10]([S:11][CH:12]([CH3:14])[CH3:13])=[C:6]2[C:5]1=[O:22])=[N+]=[N-].[C:23](OC(=O)C)(=[O:25])[CH3:24]>[C].[Pd].C(O)(=O)C>[C:23]([NH:1][CH:4]1[CH2:21][CH2:20][C:7]2=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:9][C:10]([S:11][CH:12]([CH3:14])[CH3:13])=[C:6]2[C:5]1=[O:22])(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 18388323HCID 18388323, compound

Product 1

HCID 12043500HCID 12043500, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 5-azido-4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (1.60 g), palladium-carbon (5%, 50% wet, 1.6 g), acetic acid (30 ml) and acetic anhydride (15 ml) was subjected to a catalytic reduction reaction at room temperature under 1 atm. The insoluble substances were filtered off; the filtrate was poured over water and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off to yield ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (1.30 g, 77.8%), which was then recrystallized from ethyl acetate-hexane. Colorless prisms. Melting point 170-171° C.

Workup

  1. customwas subjected to a catalytic reduction reaction at room temperature under 1 atm
  2. filtrationThe insoluble substances were filtered off
  3. additionthe filtrate was poured over water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  7. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-a390786a97b24da487c2704427cfa99d
Source dataset
uspto-grants-2002_05
Patent number
US06391905B1

Reaction notes

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