Sulfuric Acid → HCID 21487149, compound

HRID 1414360Notes

Reaction equation

HRID 1414360 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][CH2:13][CH:14]=O)[CH2:9][N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:6]=2[CH:22]=1.S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:14]=[CH:13][N:12]=[C:10]3[CH2:9][N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:6]=2[CH:22]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 178521281HCID 178521281, 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 stir at room temperature under nitrogen overnight, poured onto crushed ice and crystallized with an aqueous sodium hydroxide solution. After the product is extracted with chloroform the chloroform extract is washed with brine, dried over sodium sulfate and concentrated to an oil in vacuo. On trituration, with ethyl acetate 10.2 g. (81%) of yellow crystalline 8-bromo-6-(2-pyridyl)-4H-imidazo[1,2-a][1,4]benzodiazepine of melting point 208°-210° C. is obtained.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. customcrystallized with an aqueous sodium hydroxide solution
  4. extractionAfter the product is extracted with chloroform the chloroform
  5. extractionextract
  6. washis washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to an oil in vacuo

Sources & evidence

ORD record
ord-950ce1022de44b7a8f7b444dea59cec9
Source dataset
uspto-grants-1977_01
Patent number
US04001261

Reaction notes

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