Thionyl Chloride → 5-(4-Chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride

HRID 1473303ノート

反応式

HRID 1473303 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:18]([O-])(=[O:20])=[O:19])=[CH:13]3)=[C:4]([O:22][CH3:23])[CH:3]=1.[Na+].S(Cl)([Cl:27])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:18]([Cl:27])(=[O:20])=[O:19])=[CH:13]3)=[C:4]([O:22][CH3:23])[CH:3]=1

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 86687359Sodium 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonate

生成物 1

HCID 866873615-(4-Chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride収率 89.2%

実験手順

A round bottom flask was charged with sodium 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonate (0.137 g, 0.369 mmol) and a septum was attached and the flask flushed with N2. DMF (1.232 mL) was added followed by thionyl chloride (0.081 mL, 1.108 mmol) by syringe at rt, an exotherm was observed. The solution was maintained at rt for 1 h, and then poured into a separatory funnel containing ice. The resulting mixture was extracted with DCM (2×15 mL). The combined organic layers were washed with water (2×10 mL) and brine (1×10 mL) and dried over Na2SO4 and concentrated to give 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride (0.121 g, 0.329 mmol), which was used immediately without further purification.

後処理

  1. customthe flask flushed with N2
  2. additionDMF (1.232 mL) was added
  3. additionpoured into a separatory funnel
  4. additioncontaining ice
  5. extractionThe resulting mixture was extracted with DCM (2×15 mL)
  6. washThe combined organic layers were washed with water (2×10 mL) and brine (1×10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ed8e263e38784056a24f2134f36fa0c4
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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