Acetic Acid → 27314-97-2

HRID 967293Notes

Reaction equation

HRID 967293 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 38.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
15 °C

Procedure

To a solution containing 100 g (0.73 mole) of benzofuroxan in 223.6 g (1.5 moles) of DBU was added a solution containing 61.7 g (1.5 moles) of cyanamide in 38 ml of acetonitrile while maintaining the temperature between 20 and 25° C. The reaction mixture was stirred at that temperature for 50 hours after which it was diluted with 662 ml of acetonitrile, cooled to 15° C. and treated with 88.2 g (1.5 moles) of acetic acid. The mixture was then stirred for 18 hours at 5° C. and the resulting precipitate collected by filtration and washed twice with 100 ml of acetonitrile. The collected solid was slurried in 200 ml of water, collected, washed twice with 50 ml of water and dried under vacuum for 3 days to give 49.7 g of tirapazamine.

Workup

  1. additionwas added a solution
  2. temperaturewhile maintaining the temperature between 20 and 25° C
  3. stirringThe mixture was then stirred for 18 hours at 5° C.
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed twice with 100 ml of acetonitrile
  6. customcollected
  7. washwashed twice with 50 ml of water
  8. customdried under vacuum for 3 days

Sources & evidence

ORD record
ord-45743ebce2a445508ba65eb4f69e02f3
Source dataset
uspto-grants-2005_10
Patent number
US06953852B2

Reaction notes

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