Hydrochloric Acid → HCID 22401675, compound

HRID 260509Notes

Reaction equation

HRID 260509 reaction equation
N[C:2]1[C:10]2[C:9](=[O:11])[N:8]3[CH2:12][CH2:13][S:14][C:7]3=[N:6][C:5]=2[N:4]([CH3:15])[N:3]=1.N([O-])=O.[Na+].[ClH:20]>O>[Cl:20][C:2]1[C:10]2[C:9](=[O:11])[N:8]3[CH2:12][CH2:13][S:14][C:7]3=[N:6][C:5]=2[N:4]([CH3:15])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 22401692HCID 22401692, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22401675HCID 22401675, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a mixture of 45 ml of hydrochloric acid and 30 ml of water was dissolved 3.35 g (15.0 mmol) of Compound 13 prepared in Example 10, and 1.05 g (15.2 mmol) of sodium nitrite was added to the solution under ice-cooling, followed by stirring for 30 minutes. Then, a solution of 1.80 g (18.2 mmol) of cuprous chloride in 30 ml of hydrochloric acid 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 then washed with water, followed by recrystallization from chloroform/ethanol to give 2.64 g (73%) of Compound 24.

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. customfollowed by recrystallization from chloroform/ethanol

Sources & evidence

ORD record
ord-1912299104d54ebaab6ad3bcbf3676f7
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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