Acetic Acid → HCID 178524184, compound

HRID 2166915Notes

Reaction equation

HRID 2166915 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].C(O)(=O)C.[N:16]([O-])=O.[Na+]>O>[C:5]([C:4]1[CH:8]=[CH:9][C:10]2[NH:11][N:16]=[N:1][C:2]=2[CH:3]=1)([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 692633,4-Diaminobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 178524184HCID 178524184, compoundYield 717.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

15.2 g (0.01 mol) of 3,4-diaminobenzoic acid was dissolved in a mixed solvent composed of 100 ml of acetic acid and 50 ml of water. The solution was cooled to less than 5° C., and a solution prepared by dissolving 10 g (0.14 mol) of sodium nitrite in 30 ml of water was added dropwise with stirring. After the mixture was stirred at a room temperature for 2 hours, the precipitated crystal was filtered off. It was recrystallized from methanol to obtain 5-carboxybenzotriazole 11.7 g (72% yield). Melting point 300° C. (decomposition).

Workup

  1. temperatureThe solution was cooled to less than 5° C.
  2. customa solution prepared
  3. additionwas added dropwise
  4. stirringAfter the mixture was stirred at a room temperature for 2 hours
  5. filtrationthe precipitated crystal was filtered off
  6. customIt was recrystallized from methanol

Sources & evidence

ORD record
ord-e8916c508ef441fdb7a7a5edc94797ba
Source dataset
uspto-grants-1983_06
Patent number
US04390618

Reaction notes

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