Sulfuric Acid → N-[4-[1-(1H-imidazol-1-yl)-ethyl]-2-nitrophenyl]formamide

HRID 1723124

Reaction equation

HRID 1723124 reaction equation
[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]=[O:16])=[CH:10][CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[N+:22]([O-])([O-:24])=[O:23].[K+].[OH-].[NH4+]>>[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]=[O:16])=[C:10]([N+:22]([O-:24])=[O:23])[CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 14518360N-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]formamide

Product 1

HCID 14518362N-[4-[1-(1H-imidazol-1-yl)-ethyl]-2-nitrophenyl]formamideYield 34.6%

Procedure

(a-4) To a cooled and stirred solution of 13 parts of N-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]formamide in 92 parts of concentrated sulfuric acid was added portionwise 6.1 parts of potassium nitrate at a temperature between -5° to -10° C. Upon completion, stirring was continued for 1.50 hour at 0° C. The reaction mixture was poured into crushed ice. The whole was treated with ammonium hydroxide at 0°~-10° C. The product was extracted three times with 195 parts of dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 48 parts of 2-propanol. The product was filtered off and dried, yielding 5.4 parts (34.6%) of N-[4-[1-(1H-imidazol-1-yl)-ethyl]-2-nitrophenyl]formamide; mp. 158° C. (int. 116).

Workup

  1. temperature(a-4) To a cooled
  2. additionThe reaction mixture was poured
  3. custominto crushed ice
  4. extractionThe product was extracted three times with 195 parts of dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from 48 parts of 2-propanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-d5a74b4b641149dcab3796bec92c7aeb
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Linked notes

Loading…