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

HRID 1925707

반응식

HRID 1925707 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4fc1342cfdfe4611b700d4c23e1bcb89
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178699B2

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