Water → Methyl 3-[4-(sec-butyl)phenylsulfonamido]thiophene-2-carboxylate

HRID 1925702노트

반응식

HRID 1925702 반응식
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH2:19][CH3:20])[CH3:18].O>ClCCl>[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH2:19][CH3:20])[CH3:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 37760484-(Butan-2-yl)benzene-1-sulfonyl chloride

생성물 1

HCID 19683026Methyl 3-[4-(sec-butyl)phenylsulfonamido]thiophene-2-carboxylate수율 49.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of methyl 3-aminothiophene-2-carboxylate (0.68 g; 4.3 mmol) in pyridine (0.52 mL; 6.4 mmol) and anhydrous dichloromethane (15 mL), was added a solution of 51 (1.0 g; 4.3 mmol) in dichloromethane (3 mL). After stirring 16 hours at room temperature, the reaction was mixed with water (50 mL), and the organic phase was separated. The aqueous phase was extracted with dichloromethane (2×10 mL), and the combined organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexanes (0 to 25% v/v gradient elution) to yield the title product as a white solid (0.75 g).

후처리

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with dichloromethane (2×10 mL)
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexanes (0 to 25% v/v gradient elution)

출처 및 근거

ORD 기록
ord-ceee2b64039541bfaf48810e54d7574c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178699B2

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