Diisobutylamine → 5-Chloro-6-hydroxy-7-propyl-3-trifluoromethyl-1,2-benzisoxazole

HRID 9246

Reaktionsgleichung

Reaktionsgleichung von HRID 9246
C(NCC(C)C)C(C)C.[OH:10][C:11]1[CH:23]=[CH:22][C:14]2[C:15]([C:18]([F:21])([F:20])[F:19])=[N:16][O:17][C:13]=2[C:12]=1[CH2:24][CH2:25][CH3:26].S(Cl)([Cl:30])(=O)=O.O1C2C=CC=CC=2C=N1.S(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)C>[Cl:30][C:23]1[C:11]([OH:10])=[C:12]([CH2:24][CH2:25][CH3:26])[C:13]2[O:17][N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[C:14]=2[CH:22]=1

Komponenten

8

Edukt 5

HCID 8085Diisobutylamine2×HCID 24648Sulfuryl chlorideHCID 710731,2-BenzisoxazoleHCID 23665763Sodium BisulfiteHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

Produkt 1

HCID 1357235225-Chloro-6-hydroxy-7-propyl-3-trifluoromethyl-1,2-benzisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Diisobutylamine (0.8 ml, 0.10 eq) and 6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole (11 gm, 1.0 eq) were dissolved in toluene (275 ml) at room temperature. Slow addition of sulfuryl chloride (4.20 ml, 1.15 eq) results in a suspension which was stirred overnight. Additional diisobutylamine (total 1.6 ml, 0.4 eq) was added in four equal portions over 24 hr until no further starting benzisoxazole was detected by analytical TLC. The reaction mixture was poured into saturated sodium bisulfite (500 ml) and ethyl ether (700 ml). The phases were separated. The ether phase was washed with brine and dried over Na2SO4. The solvent was evaporated in vac to give an orange solid which was purified by chromatography on silica gel eluting with acetone:hexane (2:98) to give the title compound.

Aufarbeitung

  1. customresults in a suspension which
  2. customThe phases were separated
  3. washThe ether phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated in vac
  6. customto give an orange solid which
  7. customwas purified by chromatography on silica gel eluting with acetone:hexane (2:98)

Quellen und Nachweise

ORD-Eintrag
ord-07cdbdf55f0e4eb6803123ffb55d89c6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091230B2

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