Pentyl nitrite → HCID 11347663, compound

HRID 430664Notes

Reaction equation

HRID 430664 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]3=[N:22][CH:23]=[C:24]([CH3:25])[N:10]3[N:9]=2)=[CH:4][CH:3]=1.N(OCCCCC)=O>O1CCCC1>[CH3:25][C:24]1[N:10]2[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]2=[N:22][CH:23]=1

Participants

4

Reactant 2

HCID 10026Pentyl nitriteHCID 181831705-(4-aminophenyl)-8-methyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine

Product 1

HCID 11347663HCID 11347663, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg of 5-(4-aminophenyl)-8-methyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine is mixed in 30 ml of tetrahydrofuran with 1.32 ml of pentyl nitrite and refluxed under argon for 2 hours. After concentration by evaporation, it is chromatographed on silica gel with methylene chloride:ethanol=10:1. 136 mg of 8-methyl-5-phenyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine is obtained.

Workup

  1. temperaturerefluxed under argon for 2 hours
  2. concentrationAfter concentration
  3. customby evaporation, it
  4. customis chromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-2b451c7b91284ed09469d02bc7e47122
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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