Sodium hydride → HCID 18923517, compound

HRID 1290153Notes

Reaction equation

HRID 1290153 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[C:9]([Cl:16])=[C:10]([CH3:15])[C:11]([Cl:14])=[CH:12][CH:13]=1)=[O:6].[H-].[Na+]>CN(C)C=O>[Cl:16][C:9]1[C:10]([CH3:15])=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[N:7]1[CH2:2][CH2:3][CH2:4][C:5]1=[O:6]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 18923486HCID 18923486, compound

Product 1

HCID 18923517HCID 18923517, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3-(4-chlorobutyryl)amino-2,6-dichlorotoluene (2.80 g) in N,N-dimethylformamide (30 ml) was added sodium hydride (60% oil dispersion, 440 mg) in one portion at 5° C. The mixture was stirred for 10 minutes at 5° C. and then for 2 hours at 60° C. The cooled mixture was poured into ice water. The separated oil was extracted with dichloromethane. The organic layer was washed with water three times, dried, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give 1-(2,4-dichloro-3-methylphenyl)-2-pyrrolidinone (1.95 g).

Workup

  1. waitfor 2 hours at 60° C
  2. extractionThe separated oil was extracted with dichloromethane
  3. washThe organic layer was washed with water three times
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-fb576747a972419890c9706e2efd330c
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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