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

HRID 542865
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HRID 542865 반응식
[CH2:1]([O:3][CH2:4]Cl)[CH3:2].[OH-].[Na+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([C:29]3[NH:30][CH:31]=[CH:32][CH:33]=3)[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:12][CH:11]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:17]=[C:18]([C:29]3[N:30]([CH2:4][O:3][CH2:1][CH3:2])[CH:31]=[CH:32][CH:33]=3)[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:14][CH:15]=1
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참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 18523Chloromethyl ethyl etherHCID 3063502Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-

생성물 1

HCID 3063491Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(ethoxymethyl)-1H-pyrrol-2-yl)-수율 48%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매
HCID 241
Benzene
용매
2회
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), chloromethyl ethyl ether (0.57 g, 6 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 20 minutes. To the mixture are added water and benzene under ice-cooling, and the mixture is shaken. The benzene layer is taken, washed with water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue is subjected to silica gel column chromatography (solvent, ethyl acetate:cyclohexane=1:20) and is recrystallized from n-hexane to give 4,5-bis(4-methoxyphenyl)-2-(1-ethoxymethylpyrrol-2-yl)thiazole (1.01 g, yield: 48%).

후처리

  1. temperaturecooling
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customis recrystallized from n-hexane

출처 및 근거

ORD 기록
ord-fabfb3feb47343308388872bfba61fc4
출처 데이터셋
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04659726

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