Sodium Hydroxide → 5-Chlorosulphonyl-2-(4-ethylphenyl)thiophene

HRID 1067617노트

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HRID 1067617 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([S:14](N3C=CC=C3)(=[O:16])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[OH-].[Na+].P(Cl)(Cl)([Cl:26])=O.P(Cl)(Cl)(Cl)(Cl)Cl>CO>[Cl:26][S:14]([C:12]1[S:13][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1)(=[O:16])=[O:15]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 23445382N-[5-(4-ethylphenyl)thiophene-2-sulfonyl]pyrrole

생성물 1

HCID 234455655-Chlorosulphonyl-2-(4-ethylphenyl)thiophene

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

A solution of N-[5-(4-ethylphenyl)thiophene-2-sulfonyl]pyrrole (100 mg, 0.32 mmol) and 6 N sodium hydroxide (1 mL) in methanol (1.5 ml) was refluxed for approximately 6 h. Evaporation of solvents and drying in vacuo resulted in an oil. Phosphorus oxychloride (258 ml, 2.52 mmol) and phosphorus pentachloride (131 mg, 0.63 mmol) were added to the oil and the resulting brown suspension was heated at 50° C. for 3 h. The resulting clear brown solution was carefully added to about 20 mL of crushed ice and then extracted with ethyl acetate (3×25 mL). The combined organic layers was washed with brine (2×5 mL), dried (MgSO4) and evaporated to leave an oily residue. Flash chromatography over silica gel using 2% ethyl acetate/hexanes yielded (53 mg, 59%) of the pure ulfonyl chloride as a pale yellow oil.

후처리

  1. customEvaporation of solvents
  2. customdrying in vacuo
  3. customresulted in an oil
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe combined organic layers was washed with brine (2×5 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto leave an oily residue

출처 및 근거

ORD 기록
ord-7b81c7da9e024b2da2628722bad3792f
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248767B1

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