Potassium Carbonate → HCID 21942288, compound

HRID 2216359Notes

Reaction equation

HRID 2216359 reaction equation
CS(O[CH2:6][C@H:7]1[C@@H:9]([CH2:10]OS(C)(=O)=O)[O:8]1)(=O)=O.[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:16][C:17]1[CH:18]=[C:19]([N:20]2[CH2:10][CH:9]3[O:8][CH:7]3[CH2:6]2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115623-BromoanilineHCID 86591773HCID 86591773, compound

Product 1

HCID 21942288HCID 21942288, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5.4 g of cis-2,3-bis(methanesulfonyloxymethyl)oxirane, 2 ml of 3-bromoaniline, 4.3 g of anhydrous potassium carbonate and 30 ml of N,N-dimethylformamide was stirred under nitrogen atmosphere at 60° C. for 2 hours and at 110° C. for 2 hours. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then evaporated. The residue was purified by silica gel column chromatography with 5–10% ethyl acetate/hexane, to give 420 mg of the title compound.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate-water
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography with 5–10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0cb2c59eb93244c78d57d6d38bed98fc
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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