Acetic Acid → 27314-97-2

HRID 967292Notes

Reaction equation

HRID 967292 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>CC(C)=O>[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 42.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution containing 3.77 g (27.7 mmoles) of benzofuroxan in 8.44 g (55.4 mmoles) of DBU was added portionwise with cooling 2.33 g (55.5 mmoles) of cyanamide. The reaction mixture was stirred at room temperature for 5 days and then diluted with 26 ml of acetone and treated with 4.16 g (69.3 mmoles) of acetic acid. After stirring at room temperature overnight the mixture was further diluted with 30.2 ml of acetone and stirred at room temperature an additional 2.5 hours. The resulting precipitate was collected and washed with 50 ml of acetone and 15 ml of water and then dried under vacuum overnight to give 2.09 g of tirapazamine.

Workup

  1. additionwas added portionwise
  2. stirringAfter stirring at room temperature overnight the mixture
  3. stirringstirred at room temperature an additional 2.5 hours
  4. customThe resulting precipitate was collected
  5. washwashed with 50 ml of acetone and 15 ml of water
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-2899034eab214476962da3930b61dbaa
Source dataset
uspto-grants-2005_10
Patent number
US06953852B2

Reaction notes

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