Ethyl bromopyruvate → 2-(N-Carbethoxy-N-methylamino)methyl-4-carbethoxythiazole

HRID 1075052ノート

反応式

HRID 1075052 の反応式
[C:1]([N:6]([CH2:8][C:9]([NH2:11])=[S:10])[CH3:7])([O:3][CH2:4][CH3:5])=[O:2].Br[CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[C:1]([N:6]([CH2:8][C:9]1[S:10][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=1)[CH3:7])([O:3][CH2:4][CH3:5])=[O:2]

参加物

4

反応物 2

HCID 66144Ethyl bromopyruvateHCID 13125119(N-Carbethoxy-N-methylamino)thioacetamide

生成物 1

HCID 204021112-(N-Carbethoxy-N-methylamino)methyl-4-carbethoxythiazole

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a solution of (N-carbethoxy-N-methylamino)thioacetamide (30.7 g; 0.17 mole) [prepared in Step B] in 180 ml of absolute ethanol was added a solution of ethyl bromopyruvate (25.0 ml; 0.20 mole) in 130 ml of absolute ethanol. The reaction mixture was heated at reflux temperature for 17 hours and then evaporated under reduced pressure, and the residue was partitioned between ether and water. The organic layer was washed with water and saturated sodium chloride solution, dried, filtered and evaporated under reduced pressure to give an oil which was placed on silica gel and chromatographed using diethyl ether as the eluting solvent. The appropriate fractions yielded the title compound as an oil; TLC [Silica/CH2Cl2 :CH3CN (85:15)] gave Rf=0.50. The NMR spectrum (60 MHz) in d6 dimethyl sulfoxide gave the following resonances δ: 8.49 (s, 1H); 4.79 (s, 2H); 4.23 (m, 4H); 3.00 (s, 3H); 1.30 (q, 6H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 17 hours
  3. customevaporated under reduced pressure
  4. customthe residue was partitioned between ether and water
  5. washThe organic layer was washed with water and saturated sodium chloride solution
  6. customdried
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give an oil which
  10. customchromatographed

出典と根拠

ORDレコード
ord-74157544c7c14367ad40e01a4fa4da4f
出典データセット
uspto-grants-1983_07
特許番号
US04394508

反応ノート

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