3,4-Dichlorophenyl isocyanate → Ethyl 5-(3,4-dichlorophenylcarbamoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

HRID 1808383Notes

Reaction equation

HRID 1808383 reaction equation
[O:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:2]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][C:17]=1[Cl:25]>C1(C)C=CC=CC=1>[Cl:25][C:17]1[CH:18]=[C:19]([NH:22][C:23]([N:6]2[CH2:7][CH2:8][C:9]3[O:1][N:2]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]=3[CH2:5]2)=[O:24])[CH:20]=[CH:21][C:16]=1[Cl:15]

Participants

4

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 44558551Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

Product 1

HCID 59483856Ethyl 5-(3,4-dichlorophenylcarbamoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate (A-06) (for synthesis see above) (0.5 g, 2.55 mmol) was dissolved in toluene (25 ml), and 1,2-dichloro-4-isocyanatobenzene (0.48 g, 2.55 mmol) was added. The reaction mixture was refluxed for 2 h. Toluene was removed in vacuo, the residue was taken up in ethyl acetate and sat. sodium hydrogen carbonate solution, and the phases were separated. The aqueous phase was extracted with ethyl acetate, and then the combined organic phases were washed with sat. sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. Purification of the crude product was carried out by column chromatography (silica gel, diethyl ether/hexane 2:1). Yield: 1.2 g (>99%)

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customToluene was removed in vacuo
  3. customsat. sodium hydrogen carbonate solution, and the phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe combined organic phases were washed with sat. sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product

Sources & evidence

ORD record
ord-ae5d6781a2ce430cb1048eb6003dfb05
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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