Sodium borohydride → HCID 11267772, compound

HRID 1826688Notes

Reaction equation

HRID 1826688 reaction equation
[CH3:1][C: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][N:3]=1.[BH4-].[Na+]>ClCCl.CO.C(O)(=O)C>[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

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 22135225HCID 22135225, compound

Product 1

HCID 11267772HCID 11267772, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.69 g (10.0 millimoles) of 8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine are dissolved in a mixture of 75 ml of dichloro methane, 5 ml of methanol and 3 ml of glacial acetic acid. To the reaction mixture 0.38 g (10.0 millimoles) of sodium borohydride are added under cooling with ice-cold water in small portions. The reaction mixture is stirred at this temperature for an hour, then washed twice with 20 ml of water and 20 ml of saturated sodium chloride solution each, washed over magnesium sulfate and evaporated in vacuo. The crude product obtained is recrystallized from 50 ml of acetonitrile each. Thus 1.20 g of the desired compound are obtained, yield 71%, mp.: 124–127° C.

Workup

  1. temperatureunder cooling with ice-cold water in small portions
  2. washwashed twice with 20 ml of water and 20 ml of saturated sodium chloride solution each,
  3. washwashed over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude product obtained
  6. customis recrystallized from 50 ml of acetonitrile each

Sources & evidence

ORD record
ord-4f47f79f10d6408780b1d897c8f405d5
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

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