Ethylene Glycol → Bosentan

HRID 1020775

반응식

HRID 1020775 반응식
[OH-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]2[C:26]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[C:25](Cl)[N:24]=[C:23]([C:37]3[N:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:22]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl.CS(C)=O>[CH3:8][C:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]2[C:26]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[C:25]([O:5][CH2:4][CH2:3][OH:6])[N:24]=[C:23]([C:37]3[N:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:22]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1)([CH3:10])[CH3:9]

참가 물질

9

반응물 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 111351604-Tert-butyl-n-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide

생성물 1

HCID 104865Bosentan

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

Sodium hydroxide (26.66 g), ethylene glycol (400 mL), tetrabutylammonium bromide (10 g), 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidin-4-yl]benzenesulfonamide (100 g) and dimethylsulphoxide (400 mL) were mixed together at 25° C. The reaction mixture was heated to 60° C. to 65° C. and the mixture was stirred for 12-14 hours at 60° C. to 65° C. The reaction mixture was cooled to 25° C. followed by the addition of dichloromethane (600 mL) and de-ionized water (1000 mL). The pH of the mixture was adjusted to 2 to 3 with concentrated hydrochloric acid and the mixture was stirred for 10 minutes. The organic layer of the reaction mixture was separated. The aqueous layer was extracted with dichloromethane (200 mL). Both the organic layers were combined, washed with de-ionized water (500 mL) and the solvent was recovered. The residue was dried under vacuum at 40° C. to 50° C. to obtain bosentan.

후처리

  1. temperatureThe reaction mixture was heated to 60° C. to 65° C.
  2. stirringthe mixture was stirred for 10 minutes
  3. customThe organic layer of the reaction mixture was separated
  4. extractionThe aqueous layer was extracted with dichloromethane (200 mL)
  5. washwashed with de-ionized water (500 mL)
  6. customthe solvent was recovered
  7. customThe residue was dried under vacuum at 40° C. to 50° C.

출처 및 근거

ORD 기록
ord-8bfb742a3241403aaf99ad34d32767bb
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716477B2

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