Acetic Acid → HCID 178420195, compound

HRID 2248339Notes

Reaction equation

HRID 2248339 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. (compound 146).

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-1d00678a430e45f7a39a375552580250
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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