Hydrochloric Acid → HCID 14990560, compound

HRID 2166031Notes

Reaction equation

HRID 2166031 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[NH:8][CH:9]([CH3:11])[CH3:10].Cl.[N:22]([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>>[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([C:4]2[CH:5]=[CH:6][C:7]3[N:8]([CH:9]([CH3:10])[CH3:11])[N:22]=[N:1][C:2]=3[CH:3]=2)=[O:13])=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14990559HCID 14990559, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14990560HCID 14990560, compoundYield 100%

Procedure

To a stirred and cooled (5° C.) solution of 12.3 parts of [3-amino-4-[(1-methylethyl)amino]phenyl](4-fluorophenyl)methanone in 150 parts of a hydrochloric acid solution 6N were added 4.7 parts of sodium nitrite. Upon complete addition, stirring was continued for 1 hour at room temperature. The mixture was treated with a potassium carbonate solution to pH 9 and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 17 parts (100%) of (4-fluorophenyl) [1-(1-methylethyl)-1H-benzotriazol-5-yl]methanone as a residue (int. 3).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-64722818d6794fb993585eec258a4382
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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