Water → N-1,2-Benzisoxazol-3-yl-2-chloroacetamide

HRID 2192304Notes

Reaction equation

HRID 2192304 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH2:10])=[N:2]1.[C:11](=[O:14])([O-])[O-].[Cs+].[Cs+].BrC[C:19]([Cl:21])=O.O>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][C:11](=[O:14])[CH2:19][Cl:21])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 89602Bromoacetyl chlorideHCID 27797491,2-Benzoxazol-3-amine

Product 1

HCID 50998330N-1,2-Benzisoxazol-3-yl-2-chloroacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of benzo[d]isoxazol-3-ylamine (1 g) and cesium carbonate (2.42 g) in dry DMF (20 mL), stirred at rt, was added bromoacetyl chloride (0.62 mL) by dropwise addition. After stirring the mixture for 8 hours, the reaction was poured into water (100 mL) and the products extracted into ether (2×200 mL). The combined extracts were dried over magnesium sulfate and concentrated to dryness. The crude product was purified on silica gel using ether/isohexane (4/6) to afford the sub-titled compound as a colourless solid (0.5 g).

Workup

  1. additionby dropwise addition
  2. stirringAfter stirring the mixture for 8 hours
  3. extractionthe products extracted into ether (2×200 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified on silica gel

Sources & evidence

ORD record
ord-c18e7af76ac345d2a1f3afe9f4ea3ce6
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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