Hydrochloric Acid → 4-Methoxy-dibenzo[b,d]furan-1-sulfonyl chloride

HRID 1293465ノート

反応式

HRID 1293465 の反応式
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]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 4593564-Methoxydibenzofuran-1-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 859671024-Methoxy-dibenzo[b,d]furan-1-sulfonyl chloride

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 22229412AcOH benzene溶媒

反応条件

温度
5 °C

実験手順

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.

後処理

  1. waitThe reaction was sired at room temperature for 20 h
  2. extractionpoured water (500 ml) and extracted with ethyl acetate (3×100 ml)
  3. washThe extract was washed with water (5×100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-70bd2ef2d4e04aebb7c3cfe323b26941
出典データセット
uspto-grants-2007_07
特許番号
US07238725B2

反応ノート

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