Sulfuric Acid → HCID 21487149, compound

HRID 1730289Notes

Reaction equation

HRID 1730289 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6]1[CH2:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:9]2[CH:19]=[C:20]([Br:23])[CH:21]=[CH:22][C:8]=2[N:7]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[Br:23][C:20]1[CH:21]=[CH:22][C:8]2[N:7]3[CH:3]=[CH:4][N:5]=[C:6]3[CH2:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:9]=2[CH:19]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178495873HCID 178495873, compound

Product 1

HCID 21487149HCID 21487149, compoundYield 81%

Procedure

A solution of 15 g. (37 mmol) of [[7-bromo-5-(2-pyridyl)-3H-1,4-benzodiazepine-2-yl]amino]acetaldehyde dimethyl-acetal in 50 ml. of concentrated sulfuric acid is allowed to stirat room temperature under nitrogen overnight, poured onto crushed ice and neutralized with an aqueous sodium hydroxide solution. The product is extracted with chloroform and the chloroform washed with brine, dried oversodium sulfate and concentrated to an oil in vacuo. On trituration, 10.2 g.(81%) of 8-bromo-6-(2-pyridyl)-4H-imidazo[1,2-a][1,4]benzodiazepine, a yellow crystalline product of melting point 208°-210°, is obtained.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionThe product is extracted with chloroform
  4. washthe chloroform washed with brine
  5. dry with materialdried oversodium sulfate
  6. concentrationconcentrated to an oil in vacuo

Sources & evidence

ORD record
ord-2d8c54ea455a4e87959b4e7d359595e3
Source dataset
uspto-grants-1976_11
Patent number
US03992393

Reaction notes

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