Toluene → Cilostazol

HRID 987186ノート

反応式

HRID 987186 の反応式
[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

参加物

9

反応物 4

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

生成物 1

HCID 2754Cilostazol収率 95%

試薬・触媒・溶媒 4

HCID 24437Sodium Sulfite触媒HCID 70681Tetrabutylammonium Chloride触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b894afb89ea049d9a9aa1a3244234579
出典データセット
uspto-grants-2003_10
特許番号
US06630590B1

反応ノート

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