Water → Acetamide, N-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)-

HRID 1855713Notes

Reaction equation

HRID 1855713 reaction equation
[C:1]([NH:4][CH:5]1[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].[OH2:14].[Cl-].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([NH:4][CH:5]1[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[C:8](=[O:14])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 4976773N-(4,5,6,7-Tetrahydrobenzo[b]thiophen-4-yl)acetamide

Product 1

HCID 106675Acetamide, N-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)-

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2.15 g of N-acetyl-4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine in 12 ml of acetic acid is stirred and 3.04 g of chromium trioxide in 13.6 ml of acetic anhydride is added in 15 minutes at 10° C. to 15° C. After an hour at 20° C., 20 ml of water is added and the mixture is allowed to stand overnight. Additional water (50 ml) is added, the mixture is saturated with sodium chloride and extracted with trichloromethane (100, 150 and 50 ml volumes). The combined extract is washed with brine and then with water. The water wash is extracted with trichloromethane and the extract is combined with the main trichloromethane extract. Evaporation of the extract affords a yellow-green residue, which after trituration with ether gives 1.32 g of the title compound, m.p. 160° C. to 164° C.

Workup

  1. waitAfter an hour at 20° C.
  2. extractionextracted with trichloromethane (100, 150 and 50 ml volumes)
  3. extractionThe combined extract
  4. washis washed with brine
  5. washThe water wash
  6. extractionis extracted with trichloromethane
  7. extractionextract
  8. customEvaporation of the extract
  9. customaffords a yellow-green residue, which after trituration with ether

Sources & evidence

ORD record
ord-eb423e913163498681547abecc8e34d9
Source dataset
uspto-grants-1980_08
Patent number
US04216149

Reaction notes

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