Hydrochloric Acid → HCID 20300397, compound

HRID 2083633Notes

Reaction equation

HRID 2083633 reaction equation
N[C:2]1[C:10]2[N:9]=[N:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].[ClH:21]>O>[Cl:21][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 20300404HCID 20300404, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20300397HCID 20300397, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a stirred solution of the 4-amino-1-cyclohexylbenzotriazole (11.4 g, 0.054 mol) in 75 ml of concentrated hydrochloric acid and 75 ml of water at 5°, was slowly added 4.1 g of sodium nitrite (0.059 mol) in 15 ml of water. On completion of the addition, the reaction mixture was allowed to stir an additional 1/2 hour at 0°-5°. Next the solution was added slowly to an excess of freshly prepared cuprous chloride in 120 ml of concentrated hydrochloric acid also at 0°-5°. On completion of the addition, the reaction came to room temperature over a 21/2 hour period. Then one liter of water was added to the reaction mixture and the crude product which precipitated was collected by filtration, washed with water and air-dried. This material was purified by column chromatography to yield 6.2 g of product, m.p. 141°-144°.

Workup

  1. customat 5°
  2. additionOn completion of the addition
  3. additionOn completion of the addition
  4. customcame to room temperature over a 21
  5. custom2 hour period
  6. customthe crude product which precipitated
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customair-dried
  10. customThis material was purified by column chromatography

Sources & evidence

ORD record
ord-75f6d981bbb6439fa418207efe681930
Source dataset
uspto-grants-1978_04
Patent number
US04086242

Reaction notes

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