Ethyl formate → HCID 67429721, compound

HRID 1661087Notes

Reaction equation

HRID 1661087 reaction equation
[CH3:1]C[O-].[Na+].[NH2:5][C:6]1[C:21]([I:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:7]=1[C:8]([NH:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[O:9].C(OCC)=O>C(O)C>[Cl:23][C:19]1[CH:18]=[C:7]2[C:6](=[C:21]([I:22])[CH:20]=1)[N:5]=[CH:1][N:10]([CH:11]([CH2:12][CH2:13][CH3:14])[CH2:15][CH2:16][CH3:17])[C:8]2=[O:9]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 67429319HCID 67429319, compound

Product 1

HCID 67429721HCID 67429721, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Poured into a solution of 4.43 g of sodium ethylate in 250 cm3 of ethanol is a solution of 3.21 g of 2-amino-5-chloro-3-iodo-N-(1-propylbutyl)benzamide in 120 cm3 of ethanol then 3.3 cm3 of ethyl formate. The reaction mixture is heated under argon at reflux for 16 h. It is then cooled in order to be evaporated using a rotary evaporator under reduced pressure (5 kPa). 200 cm3 of dichloromethane and 150 cm3 of water are added, while stirring, to the concentration residue. The aqueous phase is extracted with 50 cm3 of dichloromethane. The organic phases are combined, washed with 50 cm3 of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated using a rotary evaporator under reduced pressure (5 kPa). The ochre product obtained is purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 100% dichloromethane). After concentrating the fractions under reduced pressure, 2.09 g of 6-chloro-8-iodo-3-(1-propylbutyl)quinazolin-4(3H)-one are obtained.

Workup

  1. temperatureThe reaction mixture is heated under argon
  2. temperatureat reflux for 16 h
  3. temperatureIt is then cooled in order
  4. customto be evaporated
  5. customa rotary evaporator under reduced pressure (5 kPa)
  6. addition200 cm3 of dichloromethane and 150 cm3 of water are added
  7. extractionThe aqueous phase is extracted with 50 cm3 of dichloromethane
  8. washwashed with 50 cm3 of a saturated aqueous solution of sodium chloride
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customa rotary evaporator under reduced pressure (5 kPa)
  12. customThe ochre product obtained
  13. customis purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 100% dichloromethane)
  14. concentrationAfter concentrating the fractions under reduced pressure, 2.09 g of 6-chloro-8-iodo-3-(1-propylbutyl)quinazolin-4(3H)-one
  15. customare obtained

Sources & evidence

ORD record
ord-0ce05ac4a0c64d62af680203bb03259c
Source dataset
uspto-grants-2011_10
Patent number
US08030320B2

Reaction notes

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