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

HRID 9246

반응식

HRID 9246 반응식
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

참가 물질

8

반응물 5

HCID 8085Diisobutylamine2회HCID 24648Sulfuryl chlorideHCID 710731,2-BenzisoxazoleHCID 23665763Sodium BisulfiteHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-07cdbdf55f0e4eb6803123ffb55d89c6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091230B2

연결된 노트

불러오는 중…