2-Pyrrolidone → HCID 21831310, compound

HRID 1601404Notes

Reaction equation

HRID 1601404 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].Cl[C:10]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][C:12]([CH2:25][F:26])([CH2:23][F:24])[N:11]=1>CN(C)C=O>[F:26][CH2:25][C:12]1([CH2:23][F:24])[N:11]=[C:10]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13]1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 21831324HCID 21831324, compound

Product 1

HCID 21831310HCID 21831310, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 1 ml of N,N-dimethylformamide was dissolved 62 mg of 2-pyrrolidinone and 35 mg of sodium hydride (60%) was added thereto under nitrogen stream. The mixture was stirred at room temperature for 20 minutes and 90 mg of 4-chloro-2,2-bisfluoromethyl-6-nitro-2H-1,3-benzoxazine dissolved in 2 ml of N,N-dimethylformamide was added thereto. The mixture was stirred at 45-55° C. for 5 hours. After addition of saturated saline solution, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 50 mg of 2,2-bisfluoromethyl-6-nitro-4-(2-oxo-1-pyrrolidinyl)-2H-1,3-benzoxazine represented by the following formula having a melting point of 195-198° C.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringThe mixture was stirred at 45-55° C. for 5 hours
  4. additionAfter addition of saturated saline solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated saline solution
  7. customdried
  8. distillationThe solvent was distilled off
  9. customthe resultant residue was purified

Sources & evidence

ORD record
ord-e4152c636b9f4574bf61e763dbe7480d
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

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