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Sodium Hydroxide → Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrol-2-yl)-

HRID 542864
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HRID 542864 반응식
C1(C)C=CC(S(O[CH2:11][C:12]([F:15])([F:14])[F:13])(=O)=O)=CC=1.[OH-].[Na+].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[C:29]([C:40]3[NH:41][CH:42]=[CH:43][CH:44]=3)[S:30][C:31]=2[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:23][CH:22]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]=[C:29]([C:40]3[N:41]([CH2:11][C:12]([F:15])([F:14])[F:13])[CH:42]=[CH:43][CH:44]=3)[S:30][C:31]=2[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:25][CH:26]=1
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참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 3063502Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-

생성물 1

HCID 3063472Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrol-2-yl)-수율 36%

시약·촉매·용매 3

HCID 74236
Tetrabutylammonium Bromide
촉매
HCID 241Benzene용매3회
HCID 962Water용매

실험 절차

4,5-Bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazole obtained in the same manner as described in Reference Example 6 (1.81 g, 5 mmole), 2,2,2-trifluoroethyl p-toluenesulfonate (1.27 g, 5 mmole), and tetra-n-butylammonium bromide (0.16 g, 0.5 mmole) are refluxed in two phases of benzene (20 ml) and 50% aqueous sodium hydroxide (20 ml) for 16 hours. To the mixture are added water and benzene under ice-cooling, and the mixture is shaken. The benzene layer is taken, and the aqueous layer is further extracted with benzene. The benzene layers are combined, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to give an oily residue. The oily residue is subjected to silica gel column chromatography (solvent: benzene) and then is recrystallized from n-hexane to give 4,5-bis(4-methoxyphenyl)-2-[1-(2,2,2-trifluoroethyl)pyrrol-2-yl]thiazole (0.80 g, yield: 36%).

후처리

  1. temperaturecooling
  2. extractionthe aqueous layer is further extracted with benzene
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto give an oily residue
  6. customis recrystallized from n-hexane

출처 및 근거

ORD 기록
ord-49bf1dff0b7540118d947cd6e67ad08e
출처 데이터셋
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04659726

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