Chloroacetyl chloride → HCID 9902381, compound

HRID 566877Notes

Reaction equation

HRID 566877 reaction equation
C[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([N+:22]([O-])=O)[CH:16]=2)[CH2:10][CH2:9]1.[H][H].Cl[CH2:28][C:29](Cl)=[O:30].[C:32](=O)(O)[O-].[Na+]>[Ni].C1COCC1>[C:6]1([CH3:32])[CH:5]=[CH:4][C:3]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]4[O:21][CH2:28][C:29](=[O:30])[NH:22][C:17]=4[CH:16]=3)[CH2:12][CH2:13]2)=[CH:2][CH:7]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21263910HCID 21263910, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9902381HCID 9902381, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-[4-(Methylphenyl)-piperazin-1-ylmethyl]-2-nitro-phenol (1.7 g, 5.2 mmol) is reduced with Raney nickel in 20 mL of THF under hydrogen. When the theoretical amount of hydrogen is taken up, the catalyst is removed by filtration. The THF is evaporated, and the residue is taken up in 50 mL of chloroform. Chloroacetyl chloride (0.65 g, 5.7 mmol) and sodium bicarbonate (1.6 g, 19.1 mmol) are added, and the mixture is stirred at room temperature for one-half hour, then extracted with water (3×50 mL) and dried over sodium sulfate. The solvent is evaporated, and the solid remaining is treated with excess potassium carbonate in 20 mL of chloroform at reflux overnight. Extraction with water, drying over sodium sulfate, and evaporation of the solvent gives a yellow solid. Recrystallization from ethyl acetate gives 0.27 g (16% yield) of 6-(4-p-tolyl-piperazin-1-ylmethyl)-4 H-benzo[1,4]oxazin-3-one; mp 209-212° C.

Workup

  1. customthe catalyst is removed by filtration
  2. customThe THF is evaporated
  3. extractionextracted with water (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated
  6. additionthe solid remaining is treated with excess potassium carbonate in 20 mL of chloroform
  7. temperatureat reflux overnight
  8. extractionExtraction with water
  9. dry with materialdrying over sodium sulfate, and evaporation of the solvent
  10. customgives a yellow solid
  11. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6eb68b4bb3a449e694770144a543fad9
Source dataset
uspto-grants-2001_01
Patent number
US06177422B1

Reaction notes

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