Sulfuryl chloride → 2-Methyl-1-benzothiophene-3-sulfonyl chloride

HRID 234328

반응식

HRID 234328 반응식
[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]

참가 물질

4

반응물 2

HCID 24648Sulfuryl chlorideHCID 709522-Methylbenzo(b)thiophene

생성물 1

HCID 229984492-Methyl-1-benzothiophene-3-sulfonyl chloride수율 64.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d8b958abf62240d287dc0c108adbe8d8
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594021

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