Ethylene Glycol → Bosentan

HRID 448549

반응식

HRID 448549 반응식
[K].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[C:21]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[C:20](Cl)[N:19]=[C:18]([C:32]3[N:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[N:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[OH-].[Ba+2].[OH-].[CH2:41]([OH:44])[CH2:42][OH:43].C1(C)C=CC=CC=1>O.C(O)C>[CH3:3][C:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[C:21]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[C:20]([O:43][CH2:42][CH2:41][OH:44])[N:19]=[C:18]([C:32]3[N:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[N:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[CH3:4]

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 1140Toluene2회HCID 6093286Barium hydroxide2회HCID 86650086p-Tert-butyl-n-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide potassium salt

생성물 1

HCID 104865Bosentan

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

10 gms of p-tert-butyl-N-[6-chloro-5-(2-methoxy-phenoxy)-[2,2′-bipyrimidin]-4-yl]benzenesulfonamide potassium salt and barium hydroxide (1.5 gms) were charged to a reaction vessel. Ethylene glycol (30 ml) and toluene (150 ml) were added thereto. The reaction mass was heated at a temperature of 110° C. for 2 hours. Further 1.5 gms of barium hydroxide was added and heating was continued for another 4 hours. After completion of the reaction, toluene was removed by distillation and water (150 ml) was added. The pH of the reaction mass was adjusted to a value ranging from 1 to 2 with a mixture of 1:1 HCl:water and extracted in dichloromethane. The organic layer was collected and washed with water (150 ml) and the solvent was distilled off to obtain a residue. To the residue a mixture of ethanol and water (1:1) was added and stirred. The resulting suspension was heated to reflux to obtain a clear solution. The clear solution was further cooled to 25° C. to isolate bosentan.

후처리

  1. temperatureheating
  2. customwas removed by distillation and water (150 ml)
  3. additionwas added
  4. additionranging from 1 to 2 with a mixture of 1:1 HCl
  5. extractionwater and extracted in dichloromethane
  6. customThe organic layer was collected
  7. washwashed with water (150 ml)
  8. distillationthe solvent was distilled off
  9. customto obtain a residue
  10. additionwas added
  11. temperatureThe resulting suspension was heated
  12. temperatureto reflux
  13. customto obtain a clear solution
  14. temperatureThe clear solution was further cooled to 25° C.

출처 및 근거

ORD 기록
ord-e1f3a17a4c0f465c86993396b4828e57
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481730B2

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