Hydrochloric Acid → 1-Butyl-1,2,3-benzotriazole-5-carboxylic acid

HRID 2166035Notes

Reaction equation

HRID 2166035 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]([OH:7])=[O:6].Cl.[N:17]([O-])=O.[Na+]>O>[CH2:12]([N:11]1[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=[N:17]1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 115502333-Amino-4-(butylamino)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 103310191-Butyl-1,2,3-benzotriazole-5-carboxylic acidYield 72.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled mixture of 43.7 parts of 3-amino-4-(butylamino)benzoic acid and 200 parts of a hydrochloric acid solutin 6N was added dropwise a solution of 22 parts of sodium nitrite in a small amount of water. Upon complete addition, the reaction mixture was stirred for 4 hours at 10°-20° C. The product was filtered off, washed with 30 parts of water and crystallized from a mixture of 2-propanone and ethyl acetate. The product was filtered off and dried, yielding 33.3 parts (72.6%) of 1-butyl-1H-benzotriazole-5-carboxylic acid; mp. 192.5° C. (int. 9).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringthe reaction mixture was stirred for 4 hours at 10°-20° C
  4. filtrationThe product was filtered off
  5. washwashed with 30 parts of water
  6. customcrystallized from a mixture of 2-propanone and ethyl acetate
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-1218a9f70cad4c6aa5d55b6463ac265e
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

Loading…