p-Toluenesulfonic acid → 1-(3-Methanesulfonylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 842182노트

반응식

HRID 842182 반응식
Cl.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])(=[O:5])=[O:4].[CH2:13]([O:15][C:16](=[O:30])[CH:17]([C:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][C:19](=O)[CH3:20])[CH3:14].C(N(CC)CC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH2:13]([O:15][C:16]([C:17]1[CH:18]=[C:19]([CH3:20])[N:9]([C:8]2[CH:10]=[CH:11][CH:12]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=2)[C:22]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:30])[CH3:14]

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 27351793-(Methylsulfonyl)aniline hydrochlorideHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

생성물 1

HCID 102933431-(3-Methanesulfonylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6212Chloroform용매

실험 절차

3-Methylsulfonylaniline hydrochloride (5.8 mmol, 1.2 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5.8 mmol, 144 g), triethylamine (5.8 mmol, 0.61 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in chloroform, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO44, then the solids were separated and solvents removed under vacuum. The crude material was purified over silica to yield the named product (m.p. 131° C.-133° C.).

후처리

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water, 5% sodium bicarbonate, and brine
  4. customThe organic layer was dried over NaSO44
  5. customthe solids were separated
  6. customsolvents removed under vacuum
  7. customThe crude material was purified over silica

출처 및 근거

ORD 기록
ord-0f86e40f09554b94a257b38169915d9b
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372777B1

반응 노트

불러오는 중…