Hydrochloric Acid → HCID 22565500, compound

HRID 25083Notes

Reaction equation

HRID 25083 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])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25](=[N:27][OH:28])[NH2:26].[CH:29](OCC)(OCC)OCC.Cl>>[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])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25]1[N:26]=[CH:29][O:28][N:27]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 86593811(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbamidoxime

Product 1

HCID 22565500HCID 22565500, compoundYield 75%

Conditions

Temperature
110 °C

Procedure

A mixture of 1.50 g (3.91 mmol) of the starting material XXIV and 15 ml of triethyl orthoformate in the presence of 0.05 ml of 36% hydrochloric acid was stirred at 110° C. for 30 min, then concentrated in vacuum. The residue was stirred with water, the precipitated crystals were filtered off, washed with water and recrystallized from 2-methoxyethanol to yield 1.15 g (75%) of the title compound; Mp.: 190-196° C.

Workup

  1. concentrationconcentrated in vacuum
  2. stirringThe residue was stirred with water
  3. filtrationthe precipitated crystals were filtered off
  4. washwashed with water
  5. customrecrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-f914de7750134f07ab7b06b7d42b3235
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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