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Water → ethyl 5-(aminothioxomethyl)tetrahydro-2H-1,2-oxazine-2-carboxylate

HRID 75180
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인쇄 미리보기

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HRID 75180 반응식
[C:1]([CH:3]1[CH2:8][O:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].C(N)(=[S:16])C.O>FC(F)(F)C(O)=O>[NH2:2][C:1](=[S:16])[CH:3]1[CH2:8][O:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1
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참가 물질

5

반응물 3

HCID 962WaterHCID 2723949ThioacetamideHCID 86674474HCID 86674474, 화합물2회

생성물 1

HCID 86674475ethyl 5-(aminothioxomethyl)tetrahydro-2H-1,2-oxazine-2-carboxylate

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
50 °C

실험 절차

A mixture of ethyl 5-cyanotetrahydro-2H-1,2-oxazine-2-carboxylate (i.e. the product of Step H) (0.63 g, 0.0034 mol) and thioacetamide (0.72 g, 0.0096 mol) in trifluoroacetic acid (about 2 mL) was stirred at 50° C. for 20 h. The reaction mixture was poured into water (10 mL) and extracted with diethyl ether (3×10 mL). The combined organic extracts were washed with water (10 mL), dried over magnesium sulfate, filtered and concentrated to provide an orange oil (about 0.76 g). The resulting oil was adsorbed onto Celite® (diatomaceous filter aid), and then purified by silica gel column chromatography (25% to 50% gradient of ethyl acetate in petroleum ether as eluant) to provide the title compound (0.19 g).

후처리

  1. extractionextracted with diethyl ether (3×10 mL)
  2. washThe combined organic extracts were washed with water (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9a6e94daa25f4b61b9f866def0284571
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835427B2

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