Methanol → HCID 53971866, compound

HRID 650588Notes

Reaction equation

HRID 650588 reaction equation
[CH2:1]([NH:5][C:6]([CH:8]=[C:9]1[C:17]2[CH:16]=[C:15]([C:18]([OH:20])=[O:19])[S:14][C:13]=2[CH2:12][CH2:11][CH2:10]1)=[O:7])[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.CO.[CH3:28]COC(C)=O>O>[CH2:1]([NH:5][C:6]([CH:8]=[C:9]1[C:17]2[CH:16]=[C:15]([C:18]([O:20][CH3:28])=[O:19])[S:14][C:13]=2[CH2:12][CH2:11][CH2:10]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 54084237HCID 54084237, compound

Product 1

HCID 53971866HCID 53971866, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(N-butylcarbamoyl)methylidene-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid (0.57 g), conc. sulfuric acid (H2SO4) (3 ml), and methanol (MeOH) (15 ml) was stirred at reflux for 1.5 hours. The reaction mixture was poured into a mixture of AcOEt and water. The organic layer was washed with saturated aqueous solution of NaHCO3, water and brine, and dried over MgSO4, and evaporated in vacuo. After evaporation, the resulting oil was purified by chromatography on silica gel (AcOEt-n-hexane as an eluent). The fractions including the object compound were collected and evaporated to give 4-(N-butylcarbamoyl)methylidene-2-methoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene (115.3 mg).

Workup

  1. temperatureat reflux for 1.5 hours
  2. washThe organic layer was washed with saturated aqueous solution of NaHCO3, water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customAfter evaporation
  6. customthe resulting oil was purified by chromatography on silica gel (AcOEt-n-hexane as an eluent)
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-85c385d4219a4177886d2a8e26e0d975
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

Loading…