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

HRID 1925702ノート

反応式

HRID 1925702 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ceee2b64039541bfaf48810e54d7574c
出典データセット
uspto-grants-2012_05
特許番号
US08178699B2

反応ノート

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