Ethyl Acetate → HCID 66808653, compound

HRID 607298Notes

Reaction equation

HRID 607298 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[N+:17]([C:3]1[CH:4]=[C:5]([O:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:6]=[CH:7][C:2]=1[S:27][C:24]1[CH:25]=[CH:26][C:21]([NH2:20])=[CH:22][CH:23]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 145104-AminothiophenolHCID 66808438HCID 66808438, compound

Product 1

HCID 66808653HCID 66808653, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound from Example 216A (1.86 g, 6.95 mmol), 4-aminothiophenol (0.88 g, 7.00 mmol), cesium carbonate (2.3 g, 7.00 mmol) in dimethylformamide (10 ml) was heated at 40° C. for 16 hours. Afterwards ice water (50 mL) was added to the solution and the resultant slurry was treated with ethyl acetate (100 ml). The layers were separated and the organic layer was washed with 10% sodium bicarbonate and 10% sodium chloride, and dried over anhydrous sodium sulfate. The drying agent was filtered and solvent was removed under vacuum leaving an orange oil as the title compound, (2.35 g, 92%).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 10% sodium bicarbonate and 10% sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. customsolvent was removed under vacuum

Sources & evidence

ORD record
ord-739530b84f934e4a9672bbc7777266c4
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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