Ethanol → HCID 69595739, compound

HRID 1826699Notes

Reaction equation

HRID 1826699 reaction equation
[CH:1]([C:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([CH3:26])[CH:18]=2)=[N:5][N:4]=1)=O.Cl.[NH2:28][NH:29][C:30]([NH2:32])=[O:31].C([O-])(=O)C.[Na+].C(O)C>CC(C)=O.O>[CH3:26][C:19]1[CH:18]=[C:17]([C:6]2[C:7]3[CH:13]=[C:12]4[O:14][CH2:15][O:16][C:11]4=[CH:10][C:8]=3[CH2:9][C:3]([CH:1]=[N:28][NH:29][C:30]([NH2:32])=[O:31])=[N:4][N:5]=2)[CH:22]=[CH:21][C:20]=1[N+:23]([O-:25])=[O:24]

Participants

7

Reactant 4

HCID 702EthanolHCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 22135222HCID 22135222, compound

Product 1

HCID 69595739HCID 69595739, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 3.51 g (10.0 millimoles) of 8-formyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine, 1.34 g (12.0 millimoles) of semicarbazide hydrochloride, 1.01 g (12.0 millimoles) of anhydrous sodium acetate and 100 ml of anhydrous ethanol is stirred under boiling for 6 hours. The reaction mixture is evaporated in vacuo, the residue is suspended in 100 ml of water, stirred at room temperature for half an hour, filtered and washed with 25 ml of water. The crude product thus obtained is heated to boiling in 75 ml of acetone for half an hour, cooled with icecold water, the precipitated product is filtered and washed with 10 ml of cold acetone. Thus 3.34 g of the desired compound are obtained, yield 81%, mp.: 260–264° C.

Workup

  1. customThe reaction mixture is evaporated in vacuo
  2. stirringstirred at room temperature for half an hour
  3. filtrationfiltered
  4. washwashed with 25 ml of water
  5. customThe crude product thus obtained
  6. temperatureis heated
  7. filtrationthe precipitated product is filtered
  8. washwashed with 10 ml of cold acetone

Sources & evidence

ORD record
ord-4e4c676238164e9886103c604561f3cc
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

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