Potassium Carbonate → 4-(N-Methylbenzenesulphonamidomethyl)-cinnamic acid

HRID 325956

반응식

HRID 325956 반응식
CNS(C1C=CC=CC=1)(=O)=O.BrCC1C=CC(C=CC(OCC)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:33][N:34]([CH2:44][C:45]1[CH:57]=[CH:56][C:48]([CH:49]=[CH:50][C:51]([O:53]CC)=[O:52])=[CH:47][CH:46]=1)[S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36]>O.CN(C)C=O>[CH3:33][N:34]([CH2:44][C:45]1[CH:46]=[CH:47][C:48]([CH:49]=[CH:50][C:51]([OH:53])=[O:52])=[CH:56][CH:57]=1)[S:35]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)(=[O:36])=[O:37]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 78858N-MethylbenzenesulfonamideHCID 248203732-Propenoic acid, 3-[4-(bromomethyl)phenyl]-, ethyl esterHCID 54517891ethyl 4-(N-methylbenzenesulphonamidomethyl)-cinnamate

생성물 1

HCID 540187574-(N-Methylbenzenesulphonamidomethyl)-cinnamic acid

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 5.1 g. (30 mmol) N-methylbenzenesulphonamide, 8.8 g. (33 mmol) ethyl 4-bromomethyl-cinnamate (m.p. 47° C.), 4.1 g. (30 mmol) potassium carbonate and 50 ml. dimethylformamide are heated, with stirring, for 4 days at 60° C. The reaction mixture is then cooled and stirred into cold water and the organic components extracted with diethyl ether. The ethereal solution is washed with 0.5 N aqueous sodium hydroxide solution, dried with anhydrous sodium sulphate and evaporated. The residue is recrystallized from isopropanol to give 7.9 g. (73% of theory) ethyl 4-(N-methylbenzenesulphonamidomethyl)-cinnamate; m.p. 112°-112.5° C.

후처리

  1. additionA mixture of 5.1 g
  2. temperatureThe reaction mixture is then cooled
  3. extractionthe organic components extracted with diethyl ether
  4. washThe ethereal solution is washed with 0.5 N aqueous sodium hydroxide solution
  5. dry with materialdried with anhydrous sodium sulphate
  6. customevaporated
  7. customThe residue is recrystallized from isopropanol
  8. customto give 7.9 g

출처 및 근거

ORD 기록
ord-9e93730fa90a4a03b3cafe58dafd181e
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04443477

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