Thionyl Chloride → Ethyl 1-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-thiazol-2-yl}piperidine-4-carboxylate

HRID 2221641ノート

反応式

HRID 2221641 の反応式
O[CH2:2][C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)[S:12][C:13]=2[CH3:14])=[C:5]([O:28][CH3:29])[CH:4]=1.S(Cl)([Cl:32])=O>C1(C)C=CC=CC=1>[Cl:32][CH2:2][C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)[S:12][C:13]=2[CH3:14])=[C:5]([O:28][CH3:29])[CH:4]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 69215032Ethyl 1-{4-[(4-hydroxymethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-thiazol-2-yl}piperidine-4-carboxylate

生成物 1

HCID 69217581Ethyl 1-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-thiazol-2-yl}piperidine-4-carboxylate収率 32%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of ethyl 1-{4-[(4-hydroxymethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-thiazol-2-yl}piperidine-4-carboxylate (1.35 g) and toluene (50 mL) was added thionyl chloride (0.42 g), and the mixture was heated under reflux for 2 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:4, v/v) to give ethyl 1-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-thiazol-2-yl}piperidine-4-carboxylate as colorless crystals (0.45 g, yield 32%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 98-99° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with ethyl acetate-hexane (1:4, v/v)

出典と根拠

ORDレコード
ord-f057c547397749ec8efe41f21f1ae62e
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

読み込み中…