Methanol → HCID 53971866, compound

HRID 2289425Notes

Reaction equation

HRID 2289425 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-90037f90e3a4422ca84934b996276249
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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