Sodium Carbonate → HCID 13424156, compound

HRID 1981318Notes

Reaction equation

HRID 1981318 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][C:18]([Cl:21])=[CH:17][CH:16]=2)=[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:18]1[CH:19]=[CH:20][C:15]([C:13]([C:8]2[C:7]([NH:6][C:3](=[O:4])[CH2:2][Br:1])=[C:11]([CH3:12])[O:10][N:9]=2)=[O:14])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 13424153HCID 13424153, compound

Product 1

HCID 13424156HCID 13424156, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Bromoacetyl bromide (39 g, 194 mmoles) was added slowly to a mixture of (4-amino-5-methylisoxazol-3-yl)-4-chlorophenylmethanone of Example Vb (22.9 g, 97 mmoles) in dichloromethane (200 ml) with 2N sodium carbonate (200 ml) and saturated sodium bicarbonate (300 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 34 g of a solid. The residue (3.0 g) was flash chromatographed (25% ethyl acetate:hexane) to yield 2.4 g (80%) of a solid, melting point 107°-110° C.

Workup

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

Sources & evidence

ORD record
ord-f0a28808d9ae47fbbfa0587ac75c83f8
Source dataset
uspto-grants-1985_04
Patent number
US04514410

Reaction notes

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