Water → HCID 23447909, compound

HRID 840127Notes

Reaction equation

HRID 840127 reaction equation
[CH2:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]=1[C:14]([OH:16])=O)[CH3:2].Cl.[Cl:18][CH2:19][CH2:20][CH2:21][NH2:22].C(N(CC)CC)C.O>CN(C)C=O>[Cl:18][CH2:19][CH2:20][CH2:21][NH:22][C:14]([C:4]1[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][O:7][C:3]=1[CH2:1][CH3:2])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 114690951-Propanamine, 3-chloro-, hydrochlorideHCID 135451045-Ethyl-3-phenyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 23447909HCID 23447909, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.1 g of 5-ethyl-3-phenylisoxazole-4-carboxylic acid (prepared as described in J. Org. Chem. 1985, 50, 5660-5666), 2.94 g of 3-chloropropylamine hydrochloride, 2.62 mL of 92% diethyl cianoposphonate and 4.38 mL of triethylamine in 50 mL of anhydrous dimethylformamide was stirred at room temperature for 3 hours, poured into 500 mL of water and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water, dried (sodium sulphate) and the solvent was evaporated under vacuum. The crude was purified by flash chromatography (ethyl acetate-petroleum ether 3:7) to give 3.35 g (73%) of the title compound. M.p. 75-76° C.

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (sodium sulphate)
  4. customthe solvent was evaporated under vacuum
  5. customThe crude was purified by flash chromatography (ethyl acetate-petroleum ether 3:7)

Sources & evidence

ORD record
ord-d2f4e5a817fc4c1eaa0be1465d939e6e
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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