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

HRID 75180
ノート
印刷プレビュー

反応式

HRID 75180 の反応式
[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
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

5

反応物 3

HCID 962WaterHCID 2723949ThioacetamideHCID 86674474HCID 86674474、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9a6e94daa25f4b61b9f866def0284571
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835427B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート