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Ammonia → Ethyl 4-isopropylthiazole-2-carboxylate

HRID 388656
ノート
印刷プレビュー

反応式

HRID 388656 の反応式
Br[CH2:2][C:3](=O)[CH:4]([CH3:6])[CH3:5].C(OC(C1O[S:15]C=CC=1)=O)C.[NH3:19].[CH3:20][CH2:21][O:22][C:23]([CH3:25])=[O:24]>C(O)C.O>[CH:4]([C:3]1[N:19]=[C:25]([C:23]([O:22][CH2:21][CH3:20])=[O:24])[S:15][CH:2]=1)([CH3:6])[CH3:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 108990371-Bromo-3-methylbutan-2-oneHCID 86627749Ethylthioxamate

生成物 1

HCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 962
Water
溶媒

反応条件

温度
0 °C

実験手順

A solution of compound 211 (3.5 g, 1.25 eq.) and ethylthioxamate (2.3 g, 1 eq.) in ethanol (40 mL) was heated to 80° C. for 6 hrs, and then cooled to 0° C. The reaction mixture was diluted with water and EtOAc, and then neutralized to pH 7 with NH3 (28%). The aqueous layer was extracted with EtOAc. The combined organic layers were dried over sodium sulfate and then removed under reduced pressure. The residue was purified by chromatography on silica gel to yield compound 212 as yellow oil in quantitative yield. 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.25 (d, J=6.73 Hz, 6H), 1.31 (t, J=7.24 Hz, 3H), 3.11 (hep, J=6.73 Hz, 1H), 4.35 (q, J=7.24 Hz, 2H), 7.72 (s, 1H).

後処理

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customremoved under reduced pressure
  4. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-36a223e625c64f6298159d1a01042964
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08377962B2

反応ノート

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