2-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester → Ethyl 2-(acetylamino)-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

HRID 1351242Notes

Reaction equation

HRID 1351242 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH2:16][CH2:15][C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2].S([O-])([O-])(=O)=[O:20].[Ce+4].S([O-])([O-])(=O)=O>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH2:16][C:15](=[O:20])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 986822-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl esterHCID 159684Ceric sulfate

Product 1

HCID 2830693Ethyl 2-(acetylamino)-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylateYield 29.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-Acetylamino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (140 g) in acetic acid (1.5 L) and water (1.5 L) was added gradually cerium (IV) sulfate 4 hydrate (900 g) with vigorously stirring. After the solution was stirred overnight, the solid was removed by filtration and the filtrate was concentrated. The solution was then neutralized with aqueous ammonia and extracted 3 times with ethyl acetate-tetrahydrofuran (=4:1). The organic layers were combined and evaporated in vacuo. The resulting solid was washed with tetrahydrofuran to provide the title compound (44 g) as a pale yellow solid.

Workup

  1. stirringAfter the solution was stirred overnight
  2. customthe solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. extractionextracted 3 times with ethyl acetate-tetrahydrofuran (=4:1)
  5. customevaporated in vacuo
  6. washThe resulting solid was washed with tetrahydrofuran

Sources & evidence

ORD record
ord-fb6ee0870ef94dcd9f3de61a065dd6d4
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…