Toluene → Cilostazol

HRID 1170049노트

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HRID 1170049 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH:13]1([N:19]2[C:23]([CH2:24][CH2:25][CH2:26][CH2:27]Cl)=[N:22][N:21]=[N:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])=O.[Na+].[Na+].CO.O>[CH:13]1([N:19]2[C:23]([CH2:24][CH2:25][CH2:26][CH2:27][O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]4)=[N:22][N:21]=[N:20]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

참가 물질

9

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 112187395-(4-Chlorobutyl)-1-cyclohexyl-1H-tetrazole

생성물 1

HCID 2754Cilostazol수율 95%

시약·촉매·용매 4

HCID 24437Sodium Sulfite촉매HCID 70681Tetrabutylammonium Chloride촉매HCID 887Methanol용매HCID 962Water용매

실험 절차

Into a three-necked flask having a capacity of 300 ml were introduced 10.00 g of 6-hydroxy-3,4-dihydrocarbostyril, 16.36 g of 1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole, 10.16 g of potassium carbonate, 3.00 g of tetrabutylammonium chloride, 0.05 g of sodium sulfite, 30 ml of toluene and 50 ml of water. The content of the flask was heated under reflux for 8 hours with stirring. After cooling the reaction mixture to ambient temperature, the deposited crystalline product was collected by filtration and washed with 50 ml of water. Then, the crude crystal thus obtained was introduced into 70 ml of 90% methanol cooled to 5° C., and stirred at 5° C. for 10 minutes for the sake of washing. The crystal was collected by filtration and further washed on the suction filter with 20 ml of 90% methanol cooled to 5° C. The crystal was dried to obtain 21.46 g (yield 95%) of 6-[4-(1-cyclohexyl-1,2,3,4-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril as a colorless needle-like crystalline product.

후처리

  1. customInto a three-necked flask having
  2. temperatureThe content of the flask was heated
  3. temperatureunder reflux for 8 hours
  4. filtrationthe deposited crystalline product was collected by filtration
  5. washwashed with 50 ml of water
  6. customThen, the crude crystal thus obtained
  7. temperaturecooled to 5° C.
  8. stirringstirred at 5° C. for 10 minutes for the sake
  9. washof washing
  10. filtrationThe crystal was collected by filtration
  11. washfurther washed on the suction
  12. filtrationfilter with 20 ml of 90% methanol
  13. temperaturecooled to 5° C
  14. customThe crystal was dried

출처 및 근거

ORD 기록
ord-458c7322a88d4aedbf2b0aedcaaa8e5b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825251B2

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