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

HRID 520958Notes

Reaction equation

HRID 520958 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-d7d2cfdefae049f3b99d7e3ef003af9a
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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