Cesium carbonate → HCID 117601702, compound

HRID 1773667Notes

Reaction equation

HRID 1773667 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:10]([NH2:11])=[C:9]([I:17])[CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1.[C:19](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:10]([NH:11][CH3:19])=[C:9]([I:17])[CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 117601618HCID 117601618, compound

Product 1

HCID 117601702HCID 117601702, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a flask containing 4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitroaniline (1000 mg, 2.78 mmol, 1 equiv) is added DMF (15 mL, 0.2 M) before adding cesium carbonate (1.4 gm, 4.17 mmol, 1.5 equiv.) and idomethane (260 μL, 4.17 mmol, 1.5 equiv). After an hour, the reaction was quenched with water and the reaction was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Purification was carried out by flash column chromatography to furnish 4-(3,5-dimethylisoxazol-4-yl)-2-iodo-N-methyl-6-nitroaniline (615 mg, 60%).

Workup

  1. waitAfter an hour
  2. customthe reaction was quenched with water
  3. customthe reaction was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customPurification

Sources & evidence

ORD record
ord-ba4cc276d378409aa4a111abae0d346b
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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