Sodium hydride → HCID 18923517, compound

HRID 1899970Notes

Reaction equation

HRID 1899970 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-dimethyl formamide (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-bb7632c526f74a4b805c0cf196e5bc80
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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