Water → HCID 70200011, compound

HRID 342413Notes

Reaction equation

HRID 342413 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[C:14]([NH:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][C:11]=1[OH:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:27]([CH3:31])[C:28](=O)[CH3:29].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:17]([NH:16][C:14]1[CH:15]=[C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:11]2[O:25][C:27]([CH3:31])=[C:28]([CH3:29])[C:12]=2[CH:13]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanoneHCID 54187218HCID 54187218, compound

Product 1

HCID 70200011HCID 70200011, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4-bis(benzoylamino)phenol (6.0 g), 3-chlorobutan-2-one (2.3 g) and potassium carbonate (5.0 g) in N,N-dimethylformamide (30 ml) was stirred at 70° C. for 3 hours. The reaction mixture was cooled and poured into water. The separated oil was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. To the residue was added conc. sulfuric acid (30 ml) and the mixture was stirred at 40° C. for 7 hours. The reaction mixture was cooled and poured into a mixture of ice and water. The separated oil was extracted with ethyl acetate and the extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from diethyl ether to give 5,7-bis(benzoylamino)-2,3-dimethylbenzo[b]furan (3.7 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe separated oil was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. additionTo the residue was added conc. sulfuric acid (30 ml)
  7. stirringthe mixture was stirred at 40° C. for 7 hours
  8. temperatureThe reaction mixture was cooled
  9. additionpoured into a mixture of ice and water
  10. extractionThe separated oil was extracted with ethyl acetate
  11. washthe extract was washed with brine
  12. dry with materialdried over sodium sulfate
  13. customevaporated in vacuo
  14. customThe residue was purified by column chromatography on silica gel
  15. customthe obtained oil was crystallized from diethyl ether

Sources & evidence

ORD record
ord-bf7ceed1f48f4302a0b0dc1f94d7bc7d
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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