Sulfuric Acid → Acemetacin

HRID 745856

반응식

HRID 745856 반응식
[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:33][C:34]([O:36]C(C)(C)C)=[O:35].S(=O)(=O)(O)O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.CC(C)=O>[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([O:25][CH2:33][C:34]([OH:36])=[O:35])=[O:24]

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 3715IndomethacinHCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetate

생성물 1

HCID 1981Acemetacin

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

25 g of indometacin, 10 g of potassium carbonate and 190 ml of acetone are stirred at 56° C. for 30 minutes. The mixture is cooled down to 40° C., 0.5 g of benzyltriethylammonium chloride is added, and 15.6 g of tert.-butyl chloroacetate are added dropwise. After 5 hours at 40° C. the reaction is complete (monitored by thin layer chromatography). The mixture is cooled down to 10° C. and 20 ml of concentrated sulphuric acid are then added dropwise in such a way that the temperature does not exceed 25° C. The mixture is stirred at 20° and 25° C. for 6 hours (monitored by thin layer chromatography), about 500 ml of water are added, and the solids are filtered off with suction, are dried in vacuo and are recrystallized from acetone-water.

후처리

  1. temperatureThe mixture is cooled down to 10° C.
  2. customdoes not exceed 25° C
  3. additionare added
  4. filtrationthe solids are filtered off with suction
  5. customare dried in vacuo
  6. customare recrystallized from acetone-water

출처 및 근거

ORD 기록
ord-edaf7ff4775945c1a34edf8954dd028f
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04600783

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