Nitronium tetrafluoroborate → HCID 14210633, compound

HRID 1762119Notes

Reaction equation

HRID 1762119 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:13]1)[CH3:2].F[B-](F)(F)F.[O:30]=[N+:31]=[O:32]>C(#N)C>[CH2:1]([O:3][C:4](=[O:24])[NH:5][C:6]1[C:7]([CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:20])([F:22])[F:21])[CH2:13]2)=[CH:8][CH:9]=[CH:10][C:11]=1[N+:31]([O-:32])=[O:30])[CH3:2]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 14210632HCID 14210632, compound

Product 1

HCID 14210633HCID 14210633, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 18 g of product of Step C in 180 ml of acetonitrile was cooled to -30° C. and then with stirring and under an inert atmosphere, 7.73 g of nitronium tetrafluoroborate were added in small fractions. After stirring for one hour and returning to ambient temperature, the reaction mixture was poured on to ice and extracted with methylene chloride. The extracts were washed with water, dried, taken to dryness under reduced pressure and purified by chromatography on silica (eluent: cyclohexane-ethyl acetate 7-3) to obtain 10.8 g of the expected product (RF=0.2) melting about 124° C. after crystallization from a mixture of isopropyl ether and methylene chloride (1-1).

Workup

  1. additionwere added in small fractions
  2. customreturning to ambient temperature
  3. additionthe reaction mixture was poured on to ice
  4. extractionextracted with methylene chloride
  5. washThe extracts were washed with water
  6. customdried
  7. custompurified by chromatography on silica (eluent: cyclohexane-ethyl acetate 7-3)

Sources & evidence

ORD record
ord-0cd549c8d51c4ed9a0ad50b5863119a6
Source dataset
uspto-grants-1989_05
Patent number
US04831043

Reaction notes

Loading…