Sulfuric Acid → HCID 19875852, compound

HRID 1086194Notes

Reaction equation

HRID 1086194 reaction equation
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[N+:25]([O-])([O-:27])=[O:26].[K+].[OH-].[NH4+]>>[N:1]1([CH:6]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:14]([N+:25]([O-:27])=[O:26])[CH:15]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 19875907HCID 19875907, compound

Product 1

HCID 19875852HCID 19875852, compoundYield 99.4%

Procedure

To a stirred and cooled (0° C.) mixture of 2.57 parts of intermediate 8, namely N-[4-[1-(1H-imidazol-1-yl)butyl]phenyl]acetamide and 23.0 parts of concentrated sulfuric acid were added portionwise 1.01 parts of potassium nitrate. Upon complete addition, stirring was continued for 30 minutes at 0° C. The reaction mixture was poured into crushed ice and treated with ammonium hydroxide to pH 10. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated, yielding 3 parts (99.4%) of N-[4-[1-(1H-imidazol-1-yl)butyl]-2-nitrophenyl]acetamide as a residue (interm. 9).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. additionThe reaction mixture was poured
  5. custominto crushed ice
  6. extractionThe product was extracted with trichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-11580a0e8e1c4b08920249873af61a2b
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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