Sodium Glycolate → N-[6-(2-hydroxy-ethoxy)-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfon-amide

HRID 326708

반응식

HRID 326708 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.[C:27]([O-])(=[O:30])[CH2:28][OH:29].[Na+].[Na]>C(O)CO>[OH:29][CH2:28][CH2:27][O:30][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 517347Sodium GlycolateHCID 5360545SodiumHCID 19735459N-[6-chloro-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfonamide

생성물 1

HCID 19735450N-[6-(2-hydroxy-ethoxy)-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfon-amide

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

190 mg of N-[6-chloro-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfonamide were added to a sodium glycolate solution from 46 mg of sodium in 1 ml of ethylene glycol. After a reaction period of 5 hours at 100° C., the reaction mixture was evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase was washed neutral, dried and evaporated under reduced pressure. The residue was chromatographed on silica gel with methylene chloride and ethyl acetate (4:1 v/v). There were obtained 175 mg of N-[6-(2-hydroxy-ethoxy)-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfon-amide, melting point 147°-149° C. (from methylene chloride/hexane).

후처리

  1. customAfter a reaction period of 5 hours at 100° C.
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  4. washThe organic phase was washed neutral
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica gel with methylene chloride and ethyl acetate (4:1 v/v)

출처 및 근거

ORD 기록
ord-e2b486f0faba44978e09600883630e9b
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270313

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