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

HRID 1925704

반응식

HRID 1925704 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>Cl>[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 3

HCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 1398824-t-Butylbenzenesulfonyl chloride

생성물 1

HCID 8015643Methyl 3-(4-tert-butylphenylsulfonamido)thiophene-2-carboxylate수율 92.5%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
65 °C

실험 절차

In an appropriate vessel, methyl 3-aminothiophene-2-carboxylate (2.5 g; 15.9 mmol) was combined with 4-tert-butylbenzene sulfonyl chloride (3.70 g; 15.9 mmol) and dissolved by addition of pyridine (5.00 mL; 63.2 mmol). The reaction mixture was heated at 65° C. for 2 hours cooled to room temperature, diluted with aqueous hydrochloric acid (100 mL; 2M) and extracted with dichloromethane (3×30 mL). The combined organic extracts were washed with aqueous hydrochloric acid (100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting crude solid was recrystallized from a minimal amount of isopropanol to give the title product as a yellow solid (5.2 g).

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane (3×30 mL)
  3. washThe combined organic extracts were washed with aqueous hydrochloric acid (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude solid was recrystallized from a minimal amount of isopropanol

출처 및 근거

ORD 기록
ord-99d88049fc4f408e9f63ac647e8fb6b1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178699B2

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