Methyl 3-amino-2-thiophenecarboxylate → Methyl 3-(4-tert-butylphenylsulfonamido)thiophene-2-carboxylate

HRID 1925707

反応式

HRID 1925707 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].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>N1C=CC=CC=1.ClCCl>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

参加物

5

反応物 2

HCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 1398824-t-Butylbenzenesulfonyl chloride

生成物 1

HCID 8015643Methyl 3-(4-tert-butylphenylsulfonamido)thiophene-2-carboxylate収率 66%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
40 °C

実験手順

To a solution of methyl 3-aminothiophene-2-carboxylate (0.55 g; 3.5 mmol) in pyridine (2 mL) and dichloromethane (2 mL) was added 4-tert-butylbenzenesulfonyl chloride (0.98 g; 4.2 mmol). The resulting mixture was warmed to 40° C. to aid in solubility, then stirred at room temperature for 48 hours. The reaction mixture was diluted with dichloromethane and washed with aqueous hydrochloric acid (2N). The aqueous layer was separated and extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, decanted, and filtered through a and of silica. The silica was washed with dichloromethane. The eluant was combined with hexanes and allowed to stand. After 24 hours the resulting solid product was collected by filtration to give the desired product as a white solid (817 mg).

後処理

  1. washwashed with aqueous hydrochloric acid (2N)
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. customdecanted
  6. filtrationfiltered through a and of silica
  7. washThe silica was washed with dichloromethane
  8. filtrationAfter 24 hours the resulting solid product was collected by filtration

出典と根拠

ORDレコード
ord-4fc1342cfdfe4611b700d4c23e1bcb89
出典データセット
uspto-grants-2012_05
特許番号
US08178699B2

関連ノート

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