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

HRID 542864
ノート
印刷プレビュー

反応式

HRID 542864 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide
触媒
HCID 241Benzene溶媒3 回
HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-49bf1dff0b7540118d947cd6e67ad08e
出典データセット
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04659726

反応ノート

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