Phosphorus oxychloride → Ethyl 4,5-dihydro-2-methyl-8-methylthiothieno[3,4-g]benzoxazole-6-carboxylate

HRID 1936869ノート

反応式

HRID 1936869 の反応式
[C:1]([NH:4][CH:5]1[CH2:20][CH2:19][C:8]2=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:10][C:11]([S:12][CH3:13])=[C:7]2[C:6]1=[O:21])(=O)[CH3:2].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:2][C:1]1[O:21][C:6]2[C:7]3=[C:11]([S:12][CH3:13])[S:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]3[CH2:19][CH2:20][C:5]=2[N:4]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 12043499Ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

生成物 1

HCID 12043502Ethyl 4,5-dihydro-2-methyl-8-methylthiothieno[3,4-g]benzoxazole-6-carboxylate収率 94%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.46 g), phosphorus oxychloride (3.46 g) and toluene (80 ml) was refluxed under heating for 1.5 hours; the solution obtained was concentrated under reduced pressure, diluted with a saturated aqueous solution of sodium hydrogen carbonate (200 ml) and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield ethyl 4,5-dihydro-2-methyl-8-methylthiothieno[3,4-g]benzoxazole-6-carboxylate (2.18 g, 94.0%), which was then recrystallized from ethyl acetate-hexane. Light-yellow needles. Melting point 131-132° C.

後処理

  1. temperaturewas refluxed
  2. temperatureunder heating for 1.5 hours
  3. customthe solution obtained
  4. concentrationwas concentrated under reduced pressure
  5. additiondiluted with a saturated aqueous solution of sodium hydrogen carbonate (200 ml)
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationafter which the solvent was distilled off

出典と根拠

ORDレコード
ord-6487b27ae7a84b92805a706f49b4ed16
出典データセット
uspto-grants-2002_05
特許番号
US06391905B1

反応ノート

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