Acetic Acid → 27314-97-2

HRID 967294Notes

Reaction equation

HRID 967294 reaction equation
[CH:1]1[CH:9]=[CH:8][C:7]2[C:3](=[N:4][O:5][N+:6]=2[O-:10])[CH:2]=1.C1CC[N:19]2[C:14](=[N:15]CCC2)CC1.N#CN.C(O)(=O)C>C(#N)C>[CH:1]1[CH:9]=[CH:8][C:7]2[N+:6]([O-:10])=[N:15][C:14]([NH2:19])=[N+:4]([O-:5])[C:3]=2[CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9864CyanamideHCID 68075BenzofuroxanHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 13541351127314-97-2Yield 38.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To a stirred mixture containing 1.000 kg (7.347 moles) of benzofuroxan and 2.237 kg (14.694 moles) of DBU was added a solution containing 618 g (14.694 moles) of cyanamide in 380 ml of acetonitrile while maintaining the temperature below 25° C. After stirring for 48 hours at 20-25° C. the reaction mixture was dilute with 6.620 liters of acetonitrile and cooled below 15° C. To the cooled mixture was added 882 g (14.694 moles) of acetic acid while maintaining the temperature below 15° C. After stirring overnight at 5-10° C. the precipitated product was collected by filtration and washed with acetonitrile (2×2 liters). The resulting solid was suspended in 2 liters of water, stirred about 30 minutes until a homogeneous suspension was obtained, and then filtered. The collected solid was resuspended in 2 liters of water, stirred for 20-30 minutes and filtered. The solid collected was dried to constant weight under vacuum at 50-55° C. to give 506.6 g of tirapazamine.

Workup

  1. additionwas added a solution
  2. temperaturewhile maintaining the temperature below 25° C
  3. temperaturecooled below 15° C
  4. temperaturewhile maintaining the temperature below 15° C
  5. stirringAfter stirring overnight at 5-10° C. the precipitated product
  6. filtrationwas collected by filtration
  7. washwashed with acetonitrile (2×2 liters)
  8. stirringstirred about 30 minutes until a homogeneous suspension
  9. customwas obtained
  10. filtrationfiltered
  11. stirringstirred for 20-30 minutes
  12. filtrationfiltered
  13. customThe solid collected
  14. customwas dried to constant weight under vacuum at 50-55° C.

Sources & evidence

ORD record
ord-19d33292dd2448fa9c6f38549ccf72ce
Source dataset
uspto-grants-2005_10
Patent number
US06953852B2

Reaction notes

Loading…