Chloroacetyl chloride → HCID 66646977, compound

HRID 1894717Notes

Reaction equation

HRID 1894717 reaction equation
[NH:1]1[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=[N:2]1.C(=O)(O)[O-].[Na+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>CCOC(C)=O>[Cl:15][CH2:16][C:17]([NH:9][NH:8][C:6]([C:5]1[NH:1][N:2]=[CH:3][CH:4]=1)=[O:7])=[O:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 71474941H-pyrazole-5-carbohydrazide

Product 1

HCID 66646977HCID 66646977, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 1H-pyrazole-5-carbohydrazide (102 mg, 0.81 mmol) in 7 mL AcOEt was added 1.8 mL of 1M sodium bicarbonate solution and the initial white suspension was stirred for a few minutes until it became completely clear two-phase solution. Upon cooling in an ice-water bath to it was added 0.7 ml AcOEt solution of chloroacetyl chloride (110 mg, 0.97 mmol). After stirring overnight, the reaction mixture was poured into a separatory funnel. The organic layer was separated and the aqueous layer was extracted twice with AcOEt. The combined org layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a white solid (110 mg).

Workup

  1. temperatureUpon cooling in an ice-water bath to it
  2. stirringAfter stirring overnight
  3. additionthe reaction mixture was poured into a separatory funnel
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with AcOEt
  6. dry with materialThe combined org layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3940ac25f9c4453284a9f304e19f65e3
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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