Potassium Carbonate → 3-((2-Amino-4-chlorophenyl)thio)-1-(pyrrolidin-1-yl)propan-1-one

HRID 70450

반응식

HRID 70450 반응식
C([O-])([O-])=O.[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:13][CH2:14][C:15](Cl)=[O:16].[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[SH:26]>C1COCC1.O>[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[S:26][CH2:13][CH2:14][C:15]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:16]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 120002-Amino-4-chlorobenzenethiolHCID 31268PyrrolidineHCID 84944Propanoyl chloride, 3-bromo-

생성물 1

HCID 866909953-((2-Amino-4-chlorophenyl)thio)-1-(pyrrolidin-1-yl)propan-1-one수율 50.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of K2CO3 (3.6 g, 26 mmol) in THF (20 ml) was added pyrrolidine (2.1 ml, 26 mmol) at room temperature, then the mixture was cooled to −78° C. and 3-bromopropanoyl chloride (1.0 g, 5.83 mmol) was added slowly. After it was stirred for 30 min, 2-amino-4-chlorobenzenethiol (837 mg, 5.24 mmol) was added to the mixture and the reaction was stirred at room temperature for 3 hours. The mixture was diluted with water, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0˜30% EtOAc in hexane) to yield the title compound (760 mg, 46%).

후처리

  1. stirringthe reaction was stirred at room temperature for 3 hours
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (0˜30% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-407ee69d0d2446c7b08cd2559c4e95aa
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822530B2

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