Hydrochloric Acid → 4-Methoxy-dibenzo[b,d]furan-1-sulfonyl chloride
Reaction equation
N[C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[O:7][C:6]=2[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[S:21](=[O:23])=[O:22].[ClH:24]>C(O)(=O)C.O.C(O)(=O)C.C1C=CC=CC=1>[CH3:16][O:15][C:5]1[C:6]2[O:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[C:10]=2[C:2]([S:21]([Cl:24])(=[O:23])=[O:22])=[CH:3][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 5 °C
Procedure
Intermediate 40 (400 mg, 1.87 mmol) was dissolved in glacial acetic acid (20 ml) and 17% HCl (10 ml). This solution was cooled to 5° C. and a solution of sodium nitrite (260 mg, 3.74 mmol) in water (5 ml) was added slowly during 10 min. The reaction was stirred for 1 h at 5° C. The reaction mixture was then added to a saturated solution of sulfur dioxide (generated from sodium sulfite and conc. HCl) in acetic acid: benzene (3:2) containing cupric chloride dihydrate (100 mg, 0.513 mmol). The reaction was sired at room temperature for 20 h and then poured water (500 ml) and extracted with ethyl acetate (3×100 ml). The extract was washed with water (5×100 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated to give the product as brown solid (350 mg) which was directly used to make the sulfonamide.
Workup
- waitThe reaction was sired at room temperature for 20 h
- extractionpoured water (500 ml) and extracted with ethyl acetate (3×100 ml)
- washThe extract was washed with water (5×100 ml)
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-70bd2ef2d4e04aebb7c3cfe323b26941
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238725B2
Reaction notes
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