Hydrochloric Acid → HCID 20300397, compound

HRID 2083631Notes

Reaction equation

HRID 2083631 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.[ClH:17].N([O-])=O.[Na+]>O>[Cl:17][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 g. of the 4-amino-1-cyclohexylbenzotriazole in 75 ml. of concentrated hydrochloric acid and 75 ml. of water kept at 5° C. is slowly added 4.1 g. of sodium nitrite in 15 ml. of water. On completion of the addition, the reaction mixture is allowed to stir an additional 1/2 hour at 0°-5° C. and then is added slowly to an excess of freshly prepared cuprous chloride in 120 ml. 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 ml. 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 g, m.p. = 141°-144° C, analytical sample, m.p.=146°-147° C., is recrystallized from CHCl3 /Et2O.

Workup

  1. customkept at 5° C.
  2. additionOn completion of the addition
  3. customalso at 0°-5° C
  4. additionOn completion of the addition
  5. stirringto stir
  6. customcome to room temperature over a 21
  7. custom2 hour period
  8. filtrationthe crude product is collected by filtration
  9. washwashed with water and air
  10. customdried
  11. customThe product is purified by column chromatography, yield: 6.2 g, m.p. = 141°-144° C, analytical sample, m.p.=146°-147° C.
  12. customis recrystallized from CHCl3 /Et2O

Sources & evidence

ORD record
ord-5de1323ebb1d4f70adbf1db44cf5afa9
Source dataset
uspto-grants-1978_04
Patent number
US04086242

Reaction notes

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