1-Pentene → 1-Methylbutyl 2-nitrobenzimidate

HRID 704319Notes

Reaction equation

HRID 704319 reaction equation
FS(O)(=O)=O.C(=O)=O.CC(C)=O.[CH2:13]=[CH:14][CH2:15][CH2:16][CH3:17].[N+:18]([C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[O:24])([O-:20])=[O:19].[OH-].[Na+]>C(Cl)Cl>[N+:18]([C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](=[NH:25])[O:24][CH:14]([CH3:13])[CH2:15][CH2:16][CH3:17])([O-:20])=[O:19]

Participants

7

Reactant 5

HCID 80041-PenteneHCID 118762-NitrobenzamideHCID 14798Sodium HydroxideHCID 24603Fluorosulfuric acidHCID 18522661Acetone cardice

Product 1

HCID 103540931-Methylbutyl 2-nitrobenzimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

9 g of fluorosulfonic acid was cooled to -78° C. with dry ice-acetone, 30 ml of 1-pentene was gradually dropwise added thereto under stirring. After completion of the dropwise addition, the stirring was continued at the same temperature for 15 minutes. 100 ml of methylene chloride which was previously cooled to -78° C., was added thereto, and then 15 g of 2-nitrobenzamide was added thereto at once. Then, the reaction was conducted for 12 hours under stirring while the temperature of the solution was returned to room temperature. After completion of the reaction, the reaction solution was poured into a mixture of 250 ml of a 1N sodium hydroxide aqueous solution and 100 ml of methylene chloride, which was cooled to 0° C., and then the mixture was vigorously stirred for 10 minutes. The reaction solution was extracted, and the extract was washed with water and then dried over Glauber's salt. After distillation of the solvent, the residue was purified by silica gel column chromatography to obtain 0.3 g of oily 1-methylbutyl 2-nitrobenzimidate (Intermediate Compound No. 63).

Workup

  1. additionwas gradually dropwise added
  2. additionAfter completion of the dropwise addition
  3. additionwas added
  4. waitThen, the reaction was conducted for 12 hours
  5. stirringunder stirring while the temperature of the solution
  6. customwas returned to room temperature
  7. customAfter completion of the reaction
  8. stirringthe mixture was vigorously stirred for 10 minutes
  9. extractionThe reaction solution was extracted
  10. washthe extract was washed with water
  11. dry with materialdried over Glauber's salt
  12. distillationAfter distillation of the solvent
  13. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-400bd21183ed419a9ed3b9b3b257f60c
Source dataset
uspto-grants-1991_01
Patent number
US04987135

Reaction notes

Loading…