Hydrochloric Acid → HCID 136201989, compound

HRID 2075967Notes

Reaction equation

HRID 2075967 reaction equation
C([O:8][C:9]1[C:10]([O:27][CH3:28])=[CH:11][C:12]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)=[C:13]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH:14]=1)C1C=CC=CC=1.Cl>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[OH:8][C:9]1[C:10]([O:27][CH3:28])=[CH:11][C:12]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)=[C:13]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:16])=[O:17])[CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67096464HCID 67096464, compound

Product 1

HCID 136201989HCID 136201989, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 5-benzyloxy-4-methoxy-N,N-dimethyl-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzenesulfonamide and methylene chloride (20 mL) was added titanium(IV) chloride (0.472 g) under ice-bath cooling. After stirring at room temperature overnight, 2 mol/L hydrochloric acid and methylene chloride were added to the mixture. The separated organic layer was washed with 2 mol/L hydrochloric acid and brine successively, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10%-100% ethyl acetate/hexane, gradient elution) to give the title compound (121 mg).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with 2 mol/L hydrochloric acid and brine successively
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: 10%-100% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-d8eee788688e41dbb6076ab4a037a965
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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