磺酰氯 → 2-甲基-1-苯并噻吩-3-磺酰氯

HRID 234328

反应方程式

HRID 234328 反应方程式
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[CH3:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[CH:8]=1>CN(C)C=O>[CH3:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[S:1]([Cl:5])(=[O:3])=[O:2]

参与物

4

反应物 2

HCID 24648磺酰氯HCID 709522-甲基苯并噻吩

产物 1

HCID 229984492-甲基-1-苯并噻吩-3-磺酰氯收率 64.4%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂2 次

反应条件

温度
0 °C

实验过程

Sulfuryl chloride (9.5 mmoles, 0.76 ml) was added to a stirred solution of dimethylformamide (DMF; 11.2 mmoles, 0.87 ml) at 0° C., and the resulting feint yellow solution was stirred for 20 min at 0° C. 2-Methylbenzo[b]thiophene (5.6 mmoles, 0.83 g) was then added, the reaction mixture was diluted with 2 ml of DMF, and then heated to 85° C. After 2.5 hrs at 85° C., the brown reaction mixture was cooled to ambient temperature and added to ice (≈100 ml). The aqueous phase was extracted with ethyl acetate (100 ml), and the organic phase was dried (MgSO4), filtered and concentrated to collect an orange-brown solid. Flash chromatography (4% ethyl acetate/hexanes) provided 0.89 g (64%) of 2-methylbenzo[b]thiophene-3-sulfonyl chloride as a yellow solid.

后处理

  1. temperatureheated to 85° C
  2. waitAfter 2.5 hrs at 85° C.
  3. temperaturethe brown reaction mixture was cooled to ambient temperature
  4. extractionThe aqueous phase was extracted with ethyl acetate (100 ml)
  5. dry with materialthe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto collect an orange-brown solid

来源与证据

ORD记录
ord-d8b958abf62240d287dc0c108adbe8d8
来源数据集
uspto-grants-1997_01
专利号
US05594021

关联笔记

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