Ammonium Chloride → HCID 15453526, compound

HRID 1700863Notes

Reaction equation

HRID 1700863 reaction equation
[CH3:1]C(C)([O-])C.[K+].[O:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH:30]([CH3:32])[CH3:31])[CH:24]=O.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH:30]([O:29][C:28]1[CH:27]=[CH:26][C:23]([CH:24]=[CH2:1])=[CH:22][C:21]=1[O:20][CH2:19][CH2:18][N:9]1[C:8](=[O:7])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17])([CH3:31])[CH3:32]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 15453522HCID 15453522, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15453526HCID 15453526, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

0.42 g of potassium tert-butoxide (3.75 mmol) is added portionwise to a suspension of 1.34 g of methyltriphenylphosphonium bromide (3.75 mmol) in 7.5 ml of tetrahydrofuran. The mixture is stirred for one hour at room temperature and is then cooled to 0° C. A solution of 1.20 g (3.4 mmol) of 3-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethoxy]-4-isopropoxybenzaldehyde in 7 ml of tetrahydrofuran is then introduced. The mixture is then stirred at room temperature for 16 hours, after which it is poured into saturated aqueous ammonium chloride solution. This mixture is extracted with dichloromethane, the organic phase is washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and filtered, and the solvent is evaporated off under vacuum. The residue is purified by chromatography on a column of silica (eluent: 80/20 cyclohexane/ethyl acetate). 0.77 g of a yellow oil which crystallizes is obtained:

Workup

  1. temperatureis then cooled to 0° C
  2. stirringThe mixture is then stirred at room temperature for 16 hours
  3. extractionThis mixture is extracted with dichloromethane
  4. washthe organic phase is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated off under vacuum
  8. customThe residue is purified by chromatography on a column of silica (eluent: 80/20 cyclohexane/ethyl acetate)
  9. custom0.77 g of a yellow oil which crystallizes
  10. customis obtained

Sources & evidence

ORD record
ord-f3d74ac21d47421484f16a71efe68185
Source dataset
uspto-grants-2002_02
Patent number
US06350913B1

Reaction notes

Loading…