Hydrogen Bromide → HCID 22401689, compound

HRID 260510Notes

Reaction equation

HRID 260510 reaction equation
[BrH:1].N[C:3]1[C:11]2[C:10](=[O:12])[N:9]3[CH2:13][CH2:14][S:15][C:8]3=[N:7][C:6]=2[N:5]([CH3:16])[N:4]=1.N([O-])=O.[Na+]>O>[Br:1][C:3]1[C:11]2[C:10](=[O:12])[N:9]3[CH2:13][CH2:14][S:15][C:8]3=[N:7][C:6]=2[N:5]([CH3:16])[N:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 22401692HCID 22401692, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22401689HCID 22401689, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a mixture of 52 ml of an aqueous solution of hydrogen bromide and 36 ml of water was dissolved 4.00 g (17.9 mmol) of Compound 13 prepared in Example 10, and 1.24 g (17.9 mmol) of sodium nitrite was added to the solution under ice-cooling, followed by stirring for 30 minutes. Then, a solution of 3.08 g (21.5 mmol) of cuprous bromide in 36 ml of an aqueous solution of hydrogen bromide was added thereto and the temperature of the mixture was raised slowly to room temperature, followed by stirring for one hour. The precipitated crystals were collected by filtration and washed with water. The crystals were then subjected to silica gel column chromatography and eluted with chloroform to give 3.51 g (68%) of Compound 25. The compound was recrystallized from chloroform/ethanol for purification.

Workup

  1. additionwas added to the solution under ice-
  2. temperaturecooling
  3. stirringby stirring for one hour
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-d6d5f1609ab843bc8775225de6668ad6
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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