Dimethylformamide → 1-(2-Methyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

HRID 1048613ノート

反応式

HRID 1048613 の反応式
[CH3:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[NH:12][N:11]=[N:10]1.[CH3:15]N(C)C=O.[H-].[Na+].CI>O>[CH3:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[N:12]([CH3:15])[N:11]=[N:10]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1366461851-(2-Methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one

生成物 1

HCID 898753421-(2-Methyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of the above-mentioned 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazole-5-one 10.00 g and N,N-dimethylformamide 100 mL was added 55% sodium hydride 2.30 g under ice-cooling. The mixtures were raised to room temperature and were stirred for one hour. To the reaction mixtures was added methyl iodide 3.2 mL under ice-cooling. The mixtures were raised to room temperature and were stirred for fourteen hours. To the reaction mixtures was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with 10% hydrochloric acid, water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give 1-(2-methyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Intermediate (PRC-P)”) 1.56 g.

後処理

  1. temperaturecooling
  2. customTo the reaction mixtures
  3. temperaturecooling
  4. temperatureThe mixtures were raised to room temperature
  5. stirringwere stirred for fourteen hours
  6. customTo the reaction mixtures
  7. extractionthe mixtures were extracted with ethyl acetate
  8. washThe organic layers were washed with 10% hydrochloric acid, water and saturated saline
  9. dry with materialwere dried over anhydrous magnesium sulfate
  10. concentrationwere then concentrated under reduced pressure

出典と根拠

ORDレコード
ord-403e7a438de74a10aec040243e727c0b
出典データセット
uspto-grants-2016_07
特許番号
US09380782B2

反応ノート

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