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Ammonia → Ethyl 4-isopropylthiazole-2-carboxylate

HRID 925931
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인쇄 미리보기

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HRID 925931 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

HCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 962
Water
용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4787f9dffa6945a6a38bc83c27080d6a
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284307B2

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