Tetrahydrofuran → 1-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone

HRID 542798

反応式

HRID 542798 の反応式
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.O1CCCC1.[F:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[C:21]([NH:29][CH3:30])[CH:20]=1>CCCCCC.O>[F:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](=[O:24])[CH2:12][C:11]2[N:7]([CH3:6])[N:8]=[N:9][N:10]=2)=[C:21]([NH:29][CH3:30])[CH:20]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 788251,5-DimethyltetrazoleHCID 13474393Methyl 4-fluoro-2-(methylamino)benzoateHCID 178418339Butyllithium

生成物 1

HCID 134743941-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8058Hexane溶媒

実験手順

A solution of butyl lithium in hexane (50 ml of 1.6M solution) was added slowly to a stirred mixture of 1,5-dimethyltetrazole (7.84 g) and dry tetrahydrofuran (170 ml) at 0°-5° under nitrogen. The mixture was stirred at 0°-5° for 0.5 hour and then methyl 4-fluoro-2-methylaminobenzoate (4.84 g) was added in portions at 0°-5°. The mixture was stirred at room temperature for 3 hours and then poured into water (500 ml). The resulting mixture was extracted with dichloromethane (5×60 ml). The extract was dried and evaporated to give an oil which partially solidified overnight. The solid was collected by filtration, washed with toluene and dried in vacuo to give the novel compound 1-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 132°-134°.

後処理

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. extractionThe resulting mixture was extracted with dichloromethane (5×60 ml)
  3. customThe extract was dried
  4. customevaporated
  5. customto give an oil which partially solidified overnight
  6. filtrationThe solid was collected by filtration
  7. washwashed with toluene
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-7340d66b0e6e414fb721ae3a56ac4fc4
出典データセット
uspto-grants-1987_04
特許番号
US04659718

関連ノート

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