Water → HCID 18368118, compound

HRID 379886Notes

Reaction equation

HRID 379886 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([NH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=1.C([O:21][CH2:22][C:23]1[CH:27]=[CH:26][O:25][C:24]=1[C:28](=[O:31])[CH2:29]Br)(=O)C.O>CN(C=O)C>[NH2:9][C:8]1[C:7]2[C:6](=[CH:5][C:4]([Cl:3])=[CH:11][CH:10]=2)[N:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:29]=1[C:28]([C:24]1[O:25][CH:26]=[CH:27][C:23]=1[CH2:22][OH:21])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 18367786HCID 18367786, compoundHCID 183678884-Chloro-2-[(ethoxycarbonyl)amino]benzonitrile

Product 1

HCID 18368118HCID 18368118, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% w/w dispersion in mineral oil, 390 mg, 8.8 mmol) in DMF (20 ml) was added a solution of 4-chloro-2-(ethoxycarbonylamino)benzonitrile (step 1, 2 g, 8.8 mmol) in DMF (5 ml) at 0° C. After stirring for 1 h at 0° C., 3-acetoxymethyl-2-(bromoacetyl)furan (step 1, 2.3 g, 8.8 mmol) was added and the resulting mixture was stirred at room temperature for an additional 6 h. The mixture was poured into water (100 ml), and extracted with ethyl acetate (300 ml). The organic extract was washed with saturated aqueous sodium bicarbonate (100 ml), brine (100 ml), and then dried (MgSO4) and concentrated. The residue was diluted with a mixture of ethanol (20 ml) and water (10 ml), and then potassium carbonate (ca. 2 g) was added. After stirring for 6 h, the mixture was poured into a saturated aqueous ammonium chloride (100 ml) and the mixture extracted with ethyl acetate (300 ml). The organic extract was washed with brine (100 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (2/1) to give 505 mg (16%) of the titled compound as yellow solids. Mass; M+=362

Workup

  1. stirringthe resulting mixture was stirred at room temperature for an additional 6 h
  2. extractionextracted with ethyl acetate (300 ml)
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous sodium bicarbonate (100 ml), brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. additionThe residue was diluted with a mixture of ethanol (20 ml) and water (10 ml)
  8. additionpotassium carbonate (ca. 2 g) was added
  9. stirringAfter stirring for 6 h
  10. additionthe mixture was poured into a saturated aqueous ammonium chloride (100 ml)
  11. extractionthe mixture extracted with ethyl acetate (300 ml)
  12. extractionThe organic extract
  13. washwas washed with brine (100 ml)
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated
  16. customThe residue was purified by flash column chromatography
  17. washeluting with ethyl acetate/hexane (2/1)

Sources & evidence

ORD record
ord-60bbc682541e4d8d97ab2e121a40a11e
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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