Triethylamine → HCID 67243508, compound

HRID 2421830Notes

Reaction equation

HRID 2421830 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[CH2:6][C:7]([CH3:21])=[N:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([CH3:20])[CH:12]=3)[C:4]=2[CH:3]=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26].C(N(CC)CC)C>C1CCCCC1>[C:28]1([O:27][C:25]([N:8]2[C:7]([CH3:21])=[CH:6][C:5]3[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][C:4]=3[C:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([CH3:20])[CH:12]=3)=[N:9]2)=[O:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 597463588-Chloro-4-methyl-1-(3-methyl-4-nitrophenyl)-5H-2,3-benzodiazepine

Product 1

HCID 67243508HCID 67243508, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

15 g (45.7 mmoles) of 8-chloro-4-methyl-1-(3-methyl-4-nitrophenyl)-5H-2,3-benzodiazepine are boiled in a mixture of 28.85 ml (228.5 mmoles) of phenyl chloroformate and 6.34 ml (45.7 mmoles) of triethylamine for 3.5 hours. The reaction mixture is diluted with 150 ml of cyclohexane, the solvent is decanted off the separated oily product, the residue is dissolved in dichloromethane, washed first with saturated sodium hydrogen carbonate solution, then with water and dried over anhydrous sodium sulfate. After evaporation the crude product is recrystallized from ethanol. Thus 11.86 g (58%) of the desired compound (yellow) melting at 188-190° C. are obtained.

Workup

  1. customthe solvent is decanted off the separated oily product
  2. dissolutionthe residue is dissolved in dichloromethane
  3. washwashed first with saturated sodium hydrogen carbonate solution
  4. dry with materialwith water and dried over anhydrous sodium sulfate
  5. customAfter evaporation the crude product
  6. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-7862ad1d708d4fbbbf5ae60299775246
Source dataset
uspto-grants-2011_06
Patent number
US07960375B2

Reaction notes

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