Chloroacetyl chloride → HCID 14371415, compound

HRID 2291981Notes

Reaction equation

HRID 2291981 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[N:4][O:5][C:6]=1[CH3:7].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[Cl:27][CH2:28][C:29](Cl)=[O:30]>ClCCl.O>[C:8]([C:3]1[C:2]([NH:1][C:29](=[O:30])[CH2:28][Cl:27])=[C:6]([CH3:7])[O:5][N:4]=1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 13424151HCID 13424151, compound

Product 1

HCID 14371415HCID 14371415, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (5° C.) mixture of 6.5 g of (4-amino-5-methylisoxazol-3-yl)phenylmethanone, 65 ml of 2N sodium carbonate, 163 ml of a saturated solution of sodium bicarbonate, and 150 ml of dichloromethane was added, dropwise, 5.1 ml of chloroacetyl chloride. The resulting mixture was stirred for one hour, diluted with dichloromethane and water, and separated. The organic phase was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to an oil. Flash chromatography of the oil (20% ethyl acetate/hexane as the eluent) afforded 7.15 g of N-(3-benzoyl-5-methylisoxazol-4-yl)chloroacetamide, m.p. 86°-88° C.

Workup

  1. temperatureTo a chilled
  2. additionwas added
  3. customseparated
  4. washThe organic phase was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-2c471a39b6d444d8aadb7eb272aa19a8
Source dataset
uspto-grants-1989_01
Patent number
US04800200

Reaction notes

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