Water → HCID 136335136, compound

HRID 1247015Notes

Reaction equation

HRID 1247015 reaction equation
Br[C:2]1[C:3]([OH:15])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C@H:12]([OH:14])[CH3:13])[N:8]=[CH:7]2.[N:16]([O-:18])=[O:17].[Na+].O>O1CCCC1.C(O)(=O)C>[OH:14][C@H:12]([CH3:13])[CH2:11][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([OH:15])[C:2]=2[N+:16]([O-:18])=[O:17])[CH:7]=[N:8]1

Participants

6

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 136335135HCID 136335135, compound

Product 1

HCID 136335136HCID 136335136, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Step A (6.99 g, 24.8 mmol) in a mixture of tetrahydrofuran (20 mL) and acetic acid (20 mL) was cooled in an ice bath. Sodium nitrite (5.13 g, 74.4 mol) was added and the mixture was stirred for one hour, warmed to room temperature and stirring continued for one hour. Water (200 mL) was added to the reaction mixture, which was extracted with ethyl acetate (200 mL). The organic layer was washed with aqueous saturated sodium bicarbonate (100 mL, to pH 7), dried (magnesium sulfate), filtered and saturated sodium bicarbonate (100 mL, to pH 7), dried (magnesium sulfate), filtered and evaporated to an oil (4.75 g). Purification by chromatography gave a bright yellow solid (2.96 g, 50%): mp 70–74° C.; LC/MS m/z 238.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringstirring
  3. waitcontinued for one hour
  4. extractionwas extracted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with aqueous saturated sodium bicarbonate (100 mL, to pH 7)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. dry with materialsaturated sodium bicarbonate (100 mL, to pH 7), dried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated to an oil (4.75 g)
  11. customPurification by chromatography

Sources & evidence

ORD record
ord-408d8715389b4cc28e3e6aa2aef04a87
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Reaction notes

Loading…