Methanol → HCID 69417262, compound

HRID 916964Notes

Reaction equation

HRID 916964 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=[O:15])[C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1.OS(O)(=O)=O.[CH3:31]O>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=[O:15])[C:12]([C:16]([O:18][CH3:31])=[O:17])=[CH:11][C:10]=1[C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69417477HCID 69417477, compound

Product 1

HCID 69417262HCID 69417262, compound

Procedure

In a round bottom flask fitted with a condenser, a suspension of the product from Step D (2.89 g; 7.60 mmol) in methanol (60 mL) was treated with concentrated H2SO4 (0.5 mL; cat.) and heated to reflux overnight. The reaction mixture was allowed to cool to room temperature, and the volatiles were removed in vacuo. The reaction was quenched with saturated aq. NaHCO3 solution and extracted with methylene chloride (5×). The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Trituration with methanol gave the desired product: m/e=392 (M+1).

Workup

  1. customIn a round bottom flask fitted with a condenser
  2. temperatureheated
  3. temperatureto reflux overnight
  4. customthe volatiles were removed in vacuo
  5. customThe reaction was quenched with saturated aq. NaHCO3 solution
  6. extractionextracted with methylene chloride (5×)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af1e88093d4b4bbbb3c4e7771dfa42e3
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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