Chloroform → HCID 16733971, compound

HRID 2423008Notes

Reaction equation

HRID 2423008 reaction equation
C(Cl)(Cl)[Cl:2].[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][C:12]2=O)(=[O:7])[CH3:6].S(Cl)(Cl)=O.C[N:29]([CH3:32])C=O>>[ClH:2].[C:16]([C:11]1[CH:12]=[C:32]([NH:29][C:12]2[C:11]3[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]=3)[N:15]=[CH:14][N:13]=2)[CH:18]=[CH:9][CH:10]=1)#[CH:17]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 136013901HCID 136013901, compound

Product 1

HCID 16733971HCID 16733971, compoundYield 73.6%

Conditions

Temperature
47.5 °C

Procedure

Into a 3.0 Lt four necked round bottomed flask, equipped with a mechanical stirrer, reflux condenser, pressure equalizing addition funnel and thermometer socket are charged chloroform (500 ml), 6,7-diacetoxy-4(3H)-quinazolinone (25 g) obtained from the process described in step (ii) of example (1) and dimethylformamide (3 ml). Thionyl chloride (46.2 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 to 45-50° C. then added chloroform (500 ml) and distilled out 500 ml of chloroform. Repeated the distillation process another two times with fresh chloroform. Then cooled the reaction mass to 20° C. 3-Ethynylaniline (15 g) was added and maintained for 2-3 hours at 20-25° C. Completion of the reaction is monitored by HPLC. Distilled of the solvent completely under vacuum. Cooled the reaction mass to 20-25° C. and triturated with isopropyl alcohol and filtered and washed the cake with isopropyl alcohol and dried to get N-(3-ethynylphenyl)-6,7-diacetoxy-4-quinazolinamine hydrochloride 28 g (73.6% by theory).

Workup

  1. customInto a 3.0 Lt four necked round bottomed flask, equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionaddition funnel
  4. customobtained from the process
  5. temperatureThe reaction mass was slowly heated
  6. temperatureto reflux temperature
  7. temperaturemaintained
  8. temperatureat reflux temperature for 6 hours
  9. customReaction
  10. distillationadded chloroform (500 ml) and distilled out 500 ml of chloroform
  11. temperatureThen cooled the reaction mass to 20° C
  12. addition3-Ethynylaniline (15 g) was added
  13. temperaturemaintained for 2-3 hours at 20-25° C
  14. distillationDistilled of the solvent completely under vacuum
  15. temperatureCooled the reaction mass to 20-25° C.
  16. customtriturated with isopropyl alcohol
  17. filtrationfiltered
  18. washwashed the cake with isopropyl alcohol
  19. customdried

Sources & evidence

ORD record
ord-cd81fb1aeee743c4a80735b3184493ae
Source dataset
uspto-grants-2011_06
Patent number
US07960545B2

Reaction notes

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