Water → HCID 11176479, compound

HRID 1826689Notes

Reaction equation

HRID 1826689 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)=[N:4][NH:3]1.O.Cl[CH2:28]Cl.[C:30](=[O:33])([O-])[O-].[Na+].[Na+]>C(OC(=O)C)(=O)C>[C:30]([N:3]1[CH:2]([CH3:1])[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)=[N:4]1)(=[O:33])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 11267772HCID 11267772, compound

Product 1

HCID 11176479HCID 11176479, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

1.70 g (5.0 millimoles) of (±)-7,8-dihydro-8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine are stirred in 10 ml of acetic anhydride at room temperature for a day. The reaction mixture is poured into a mixture of 100 ml of water and 75 ml of dichloro methane, stirred for an hour and the pH is adjusted to 8 by adding sodium carbonate in portions. The layers are separated, the aqueous phase is extracted twice with 25 ml of dichloro methane each. The united organic phases are washed with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The crude product obtained is recrystallized from 15 ml of ethanol. Thus 1.65 g of the desired product are obtained, yield 87%, mp.: 178–181° C.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted twice with 25 ml of dichloro methane each
  3. washThe united organic phases are washed with 50 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude product obtained
  7. customis recrystallized from 15 ml of ethanol

Sources & evidence

ORD record
ord-6ac5d405b2264ecd8e0204313f450fac
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

Loading…