Sodium Carbonate → HCID 20265410, compound

HRID 1981316Notes

Reaction equation

HRID 1981316 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH2:6][C:7]1[C:8]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])=[O:14])=[N:9][O:10][C:11]=1[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.O>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]([C:8]1[C:7]([NH:6][C:3](=[O:4])[CH2:2][Br:1])=[C:11]([CH3:12])[O:10][N:9]=1)=[O:14]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 13424152HCID 13424152, compound

Product 1

HCID 20265410HCID 20265410, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Bromoacetylbromide (42 g, 210 mmoles) was added slowly to a mixture of (4-amino-5-methylisoxazol-3-yl)-2-chlorophenylmethanone of Example IIIb (24.8 g, 105 mmoles) in dichloromethane (300 ml) with 2N sodium carbonate (200 ml) and saturated sodium bicarbonate (500 ml) at 5° C. After stirring for 1 hour, the mixture was diluted with dichloromethane (400 ml) and water (400 ml). The organics were washed with water, saturated sodium chloride, dried (sodium sulfate) and evaporated to give 36 g of an oil. The residue (5.2 g) was flash chromatographed (25% ethyl acetate:hexane) to yield 4.5 g (85%) of an oil.

Workup

  1. washThe organics were washed with water, saturated sodium chloride
  2. dry with materialdried (sodium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-35e404a367c244d99c80dfdb4b9f8e61
Source dataset
uspto-grants-1985_04
Patent number
US04514410

Reaction notes

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