Acetic Acid → HCID 178420195, compound

HRID 466623Notes

Reaction equation

HRID 466623 reaction equation
[N:1]1([CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)(=O)C.[N:25]([O-])=O.[Na+].C(=O)([O-])O.[Na+]>O>[N:1]1([CH:6]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:7]2[CH:12]=[CH:11][C:10]3[NH:13][N:25]=[N:14][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 14990928HCID 14990928, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178420195HCID 178420195, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred and cooled (5° C.) solution of 5.2 parts of 4-[(1H-imidazol-1-yl)phenylmethyl]-1,2-benzenediamine in 4.8 parts of acetic acid and 20 parts of water was added a solution of 1.38 parts of sodium nitrite in 10 parts of water. The whole was stirred for 1 hour at room temperature. The reaction mixture was treated with a sodium hydrogen carbonate solution and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 64 parts of ethyl acetate. The product was filtered off and dried. yielding 4.7 parts (85.3%) of 5-[(1H-imidazol-1-yl)phenylmethyl]-1H-benzotriazole; mp. 178.8° C. (comp. 35).

Workup

  1. stirringThe whole was stirred for 1 hour at room temperature
  2. extractionthe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 64 parts of ethyl acetate
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-146d3522ba0542658fb21dfde6ac85c5
Source dataset
uspto-grants-1992_10
Patent number
US05157046

Reaction notes

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