Water → HCID 21129695, compound

HRID 1370256Notes

Reaction equation

HRID 1370256 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH2:12][CH:11]([C:13](Cl)=[O:14])[O:10][N:9]=2)[CH:3]=1.C(N(CC)CC)C.[OH:23][N:24]=[C:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1.O>C1COCC1>[OH:23]/[N:24]=[C:25](\[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)/[C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:13]([CH:11]2[O:10][N:9]=[C:8]([C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)[CH2:12]2)=[O:14])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 346729HCID 346729, compoundHCID 18510746HCID 18510746, compound

Product 1

HCID 21129695HCID 21129695, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled stirred suspension of (±)-4,5-dihydro-3-(3-pyridinyl)-5-isoxazole carbonylchloride monohydrochloride (0.016 mol) in dry THF (100 ml), triethylamine (0.040 mol) was added. The reaction mixture was cooled to 0° C. 4-[(Hydroxyimino)phenylmethyl]benzeneamine (0.018 mol) was added in one portion. Stirring was continued for 2.5 hours. Water was added to the reaction mixture and this mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was stirred in CH3OH/CH2Cl2 5/95. The precipitate was filtered off, washed with CH3OH/CH2Cl2 5/95 and dried. The product (1.6 g) was stirred in boiling ethyl acetate (25 ml) and crystallized from ethyl acetate (150 ml). The volume was reduced to 75 ml. The precipitate was filtered off, washed with ethyl acetate and DIPE, then dried, yielding 0.8 g of (±)-(E)-4,5-dihydro-N-[4-[(hydroxyimino)phenylmethyl]phenyl]-3-(3-pyridinyl)-5-isoxazolecarboxamide. (compound 301)

Workup

  1. additionwas added
  2. stirringStirring
  3. extractionthis mixture was extracted with CH2Cl2
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. stirringThe residue was stirred in CH3OH/CH2Cl2 5/95
  9. filtrationThe precipitate was filtered off
  10. washwashed with CH3OH/CH2Cl2 5/95
  11. customdried
  12. stirringThe product (1.6 g) was stirred
  13. customcrystallized from ethyl acetate (150 ml)
  14. filtrationThe precipitate was filtered off
  15. washwashed with ethyl acetate and DIPE
  16. customdried

Sources & evidence

ORD record
ord-accd360c7be7460585571f5ca7b940e4
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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