Potassium Carbonate → 213978-36-0

HRID 1603206Notes

Reaction equation

HRID 1603206 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7]Br)[C:3](Br)=[O:4].[NH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:1][CH:2]1[CH2:6][CH2:7][N:9]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133964-AminobenzonitrileHCID 112898262,4-dibromobutanoyl Bromide

Product 1

HCID 9860086213978-36-0

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,4-Dibromobutyryl bromide (BBBB, 12.13 g, 0.039 mole) was added via an addition funnel to a cold (5° C.), well stirred slurry of 4-aminobenzonitrile (4-ABN, 4.0 g, 0.034 mole), Na3PO4 (3.05 g, 0.019 mole) and acetonitrile (42 mL) while maintaining a temperature below 30° C. during the addition. The addition funnel was rinsed with acetonitrile (2 mL). Upon completion of the coupling (determined by LC), K2CO3 (9.36 g, 0.069 mole) was added via an addition funnel while maintaining the reaction temperature below 30° C. Upon completion of the reaction (determined by LC), the slurry was filtered. The flask and the cake were washed with acetonitrile (40 mL). The filtrate and the wash were combined to afford a solution of 4-(3-bromo-2-oxopyrrolidin-1-yl)benzonitrile in acetonitrile. Qualitative LC analysis showed the product with 96.1 area % purity.

Workup

  1. temperaturewhile maintaining a temperature below 30° C.
  2. additionduring the addition
  3. washThe addition funnel was rinsed with acetonitrile (2 mL)
  4. temperaturewhile maintaining the reaction temperature below 30° C
  5. customUpon completion of the reaction (determined by LC)
  6. filtrationthe slurry was filtered
  7. washThe flask and the cake were washed with acetonitrile (40 mL)

Sources & evidence

ORD record
ord-4ec0b66f233a4d23bb4fb239cb8891d6
Source dataset
uspto-grants-1999_11
Patent number
US05986107

Reaction notes

Loading…