Phosphorus tribromide → HCID 21866673, compound

HRID 1796405Notes

Reaction equation

HRID 1796405 reaction equation
P(Br)(Br)Br.[CH3:5][C:6]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[N:20]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[O:22][C:23]=1[CH3:24])([CH3:11])[C:7]([NH:9]O)=O.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[CH3:11][C:6]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[N:20]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[O:22][C:23]=1[CH3:24])([CH3:5])[C:7]#[N:9]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 21866788HCID 21866788, compound

Product 1

HCID 21866673HCID 21866673, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosphorus tribromide (6.77 g) was added to 94 ml of a solution of 4.90 g of 2-methyl-2-{6-[5-methyl-2-(p-tolyl)oxazol-4-yl]hexyloxy}propionohydroxamic acid in benzene, and heated to reflux for 4 hours. The reaction solution was cooled, poured into ice-cold water. After addition of saturated aqueous sodium hydrogencarbonate solution, the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=9:1) to provide 3.32 g of the objective compound as a colorless crystals. M.p. 36° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine sequentially
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-1ec758c10229427fbadfaea4f2939ab8
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Reaction notes

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