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

HRID 70450

反応式

HRID 70450 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-407ee69d0d2446c7b08cd2559c4e95aa
出典データセット
uspto-grants-2014_09
特許番号
US08822530B2

関連ノート

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