Hydrochloric Acid → HCID 21220850, compound

HRID 1584793Notes

Reaction equation

HRID 1584793 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[C:15]2[O:14][CH:13]=[CH:12][C:11]=2[CH:10]=[C:9]([N:16]2[C:20]([C:21]([F:24])([F:23])[F:22])=[N:19][N:18]=[N:17]2)[CH:8]=1.Cl>O1CCCC1>[F:24][C:21]([F:22])([F:23])[C:20]1[N:16]([C:9]2[CH:8]=[C:7]([CH:2]=[O:1])[C:15]3[O:14][CH:13]=[CH:12][C:11]=3[CH:10]=2)[N:17]=[N:18][N:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21220891HCID 21220891, compound

Product 1

HCID 21220850HCID 21220850, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-([1,3]-Dioxan-2-yl)-5-(5-trifluoromethyl-tetrazol-1-yl)-benzofuran (160 mg) was dissolved in tetrahydrofuran (30 ml) and dilute hydrochloric acid (20 ml; 2M). The reaction mixture was heated to reflux and stirred for a total of 3 h, cooled and concentrated in vacuo. The residue was taken up in chloroform (40 ml), and the organic phase washed with 8% sodium bicarbonate solution (3×20 ml), dried and concentrated in vacuo. The crude material was purified by FCC eluted with dichloromethane-hexane (1:1) to dichloromethane-hexane (2:1) to give the title compound (100 mg) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. washthe organic phase washed with 8% sodium bicarbonate solution (3×20 ml)
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by FCC
  9. washeluted with dichloromethane-hexane (1:1) to dichloromethane-hexane (2:1)

Sources & evidence

ORD record
ord-efa5215072614c969ea39bdbeb430386
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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