Potassium Carbonate → HCID 68948398, compound

HRID 2384897Notes

Reaction equation

HRID 2384897 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15]Cl)=[C:9]([O:18][CH3:19])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:9]([O:18][CH3:19])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 68950115HCID 68950115, compound

Product 1

HCID 68948398HCID 68948398, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Add pyrrolidine (7.5 mL, 90 mmol) to a mixture of N-(4-bromo-2-methoxy-phenyl)-2-chloro-acetamide (5.0 g, 18 mmol) and potassium carbonate (4.96 g, 36 mmol) in acetonitrile (180 mL). Heat the mixture at 80° C. for 4 h. Cool the mixture to RT and filter with CH2Cl2 (300 mL). Wash the filtrate with brine (400 mL), back extract the aqueous twice with CH2Cl2 (300 mL). Wash the combined organic layer with water (250 mL). Dry the organic portion over Na2SO4, filter, and concentrate. Dry the resulting solid on house vacuum overnight to give 5.6 g (99%) of the title compound. LC-ES/MS m/z (81Br) 314.0 [M+].

Workup

  1. temperatureCool the mixture to RT
  2. filtrationfilter with CH2Cl2 (300 mL)
  3. washWash the filtrate with brine (400 mL)
  4. extractionback extract the aqueous twice with CH2Cl2 (300 mL)
  5. washWash the combined organic layer with water (250 mL)
  6. dry with materialDry the organic portion over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customDry the resulting solid on house vacuum overnight

Sources & evidence

ORD record
ord-7a7a5c6bd9114e5087811d2282b93b81
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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