Boron trifluoride → 4-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenol

HRID 732237

反応式

HRID 732237 の反応式
[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1)([CH3:3])[CH3:2].Br(O)(=O)=O.[C-]#N.[Na+].B(F)(F)F>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C.CS(C)=O.C(O)(=O)C>[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)([CH3:3])[CH3:2]

参加物

9

反応物 4

HCID 6356Boron trifluorideHCID 8929Sodium CyanideHCID 24445Bromic acidHCID 578383635-Isopropyl-4-(4-Methoxy-Phenyl)-2-Methyl-1,3-Thiazole

生成物 1

HCID 162024444-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenol

試薬・触媒・溶媒 4

HCID 67553Tetrabutylammonium Iodide触媒HCID 176Acetic Acid溶媒HCID 679Dimethyl Sulfoxide溶媒HCID 3283Diethyl Ether溶媒

実験手順

In the fourth step, the compound (5) prepared in the third step is reacted with bromic acid and acetic acid, sodium cyanide and dimethylsulfoxide, or tetrabutylammonium iodide and boron trifluoride.diethylether, to afford 4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)-phenol (6). Conventionally, ethanethiol is used, whereby offensive odors occur and reagent handling is difficult to the extent of being unsuitable for use in mass production. However, in the present invention, the use of the compound (5) and the above materials reacting therewith, in particular, bromic acid and acetic acid result in decreased offensive odors, low price, simple reagent handling and a drastically increased preparation yield (yield: 84%).

出典と根拠

ORDレコード
ord-125362ffe0174e0bb4b5bb8def022a0f
出典データセット
uspto-grants-2009_09
特許番号
US07585979B2

関連ノート

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