Chloroform → 4-Chloroquinazoline-6,7-diyl diacetate

HRID 2423005Notes

Reaction equation

HRID 2423005 reaction equation
[CH:1]([Cl:4])(Cl)Cl.[C:5]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][C:20](=[O:22])[CH3:21])[N:15]=[CH:14][NH:13]C2=O)(=[O:7])[CH3:6].C(Cl)(=O)C(Cl)=O>CN(C)C=O>[Cl:4][C:1]1[C:11]2[C:16](=[CH:17][C:18]([O:19][C:20](=[O:22])[CH3:21])=[C:9]([O:8][C:5](=[O:7])[CH3:6])[CH:10]=2)[N:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 65578Oxalyl chlorideHCID 136013901HCID 136013901, compound

Product 1

HCID 272813774-Chloroquinazoline-6,7-diyl diacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

Into a 3.0 L four necked round bottomed flask, equipped with a mechanical stirrer, reflux condenser, pressure equalizing addition funnel and thermometer socket are charged chloroform (1000 ml), 6,7-diacetoxy-4(3H)-quinazolinone (50 g) obtained by the process described in step (ii) above and dimethylformamide (2 ml). Oxalyl chloride (50 g) was slowly added in about 20-30 minutes. The reaction mass was slowly heated to reflux temperature and maintained at reflux temperature for 6 hours. Reaction was found to be over by HPLC. Cooled the reaction mass to 25-30° C. and slowly quenched into saturated sodium bicarbonate solution at less than 10° C. Separated the organic layer and dried over anhydrous sodium sulfate. The dried organic layer thus obtained was directly used in the next step without any purification.

Workup

  1. temperaturereflux condenser
  2. additionaddition funnel
  3. customobtained by the process
  4. temperatureThe reaction mass was slowly heated
  5. temperatureto reflux temperature
  6. temperaturemaintained
  7. temperatureat reflux temperature for 6 hours
  8. customReaction
  9. customslowly quenched into saturated sodium bicarbonate solution at less than 10° C
  10. customSeparated the organic layer
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe dried organic layer thus obtained
  13. customwas directly used in the next step without any purification

Sources & evidence

ORD record
ord-1589c0cbaf6e464e92e1365ed6d00238
Source dataset
uspto-grants-2011_06
Patent number
US07960545B2

Reaction notes

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