Hydrochloric Acid → HCID 20300397, compound

HRID 1733161Notes

Reaction equation

HRID 1733161 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 11.4 grams of the 4-amino-1-cyclohexylbenzotriazole in 75 milliliters of concentrated hydrochloric acid and 75 milliliters of water at 5° C. is slowly added 4.1 grams of sodium nitrite in 15 milliliters of water. On completion of the addition, the reaction mixture is allowed to stir an additional 1/2 hour at 0°-5° C. Next the solution is added slowly to an excess of freshly prepared cuprous chloride in 120 milliliters of concentrated hydrochloric acid also at 0°-5° C. On completion of the addition, the reaction is allowed to stir and come to room temperature over a 21/2 hour period. Then 1000 milliliters of water is added to the reaction mixture and the crude product is collected by filtration, washed with water and air dried. The product is purified by column chromatography, yield: 6.2 gram, m.p.=141°-144° C. The analytical sample, m.p.=146°-147° C., is recrystallized from CHCl3 /Et2O.

Workup

  1. customat 5° C.
  2. additionOn completion of the addition
  3. additionOn completion of the addition
  4. stirringto stir
  5. customcome to room temperature over a 21
  6. custom2 hour period
  7. filtrationthe crude product is collected by filtration
  8. washwashed with water and air
  9. customdried
  10. customThe product is purified by column chromatography, yield: 6.2 gram, m.p.=141°-144° C
  11. customThe analytical sample, m.p.=146°-147° C., is recrystallized from CHCl3 /Et2O

Sources & evidence

ORD record
ord-648f299ecd90449f8d02593c66dd1926
Source dataset
uspto-grants-1980_12
Patent number
US04240822

Reaction notes

Loading…