Dimethylformamide → HCID 54384707、化合物

HRID 1004365ノート

反応式

HRID 1004365 の反応式
[CH3:1][N:2]([CH3:5])C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:12][O:13][N:14]=[C:15]([C:32]1[NH:36][N:35]=[N:34][N:33]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31].S(OC)(OC)(=O)=O>CCOCC>[CH3:12][O:13][N:14]=[C:15]([C:32]1[N:36]([CH3:1])[N:35]=[N:34][N:33]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31].[CH3:12][O:13][N:14]=[C:15]([C:32]1[N:33]=[N:34][N:2]([CH3:5])[N:36]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178502648HCID 178502648、化合物

生成物 2

HCID 54384707HCID 54384707、化合物収率 37.9%HCID 54527829HCID 54527829、化合物収率 19%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

N,N-Dimethylformamide (3 ml) and potassium carbonate (0.33 g, 2.4 mmol) were added to 2-(2,5-dimethylphenoxymethyl)phenyl 1H-tetrazol-5-yl ketone O-methyloxime (0.40 g, 1.2 mmol), and the mixture was stirred at room temperature for 5 minutes. Then, dimethyl sulfate (0.23 g, 1.8 mmol) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, ether (150 ml) was added, and the mixture was washed with brine (50 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl 1-methyl-1H-tetrazol-5-yl ketone O-methyloxime as colorless crystals (0.16 g, 37.9%) [mp. 115.5-116.5° C.; 1H-NMR(CDCl3) δ ppm: 1.97(3H,s), 2.26(3H,s), 4.06(3H,s), 4.13(3H,s), 4.89(2H,s), 6.50(1H,s), 6.65(1H,d,J=7.9), 6.97(1H,d,J=7.9), 7.34-7.58(4H,m)] and 2-(2,5-dimethylphenoxymethyl)phenyl 2-methyl-2H-tetrazol-5-yl ketone O-methyloxime as colorless crystals (0.08 g, 19.0%) [mp. 131-132° C.; 1H-NMR(CDCl3) δ ppm: 2.12(3H,s), 2.24(3H,s), 4.09(3H,s), 4.34(3H,s), 4.96(2H,s), 6.54(1H,s), 6.64(1H,d,J=7.9), 6.98(1H,d,J=7.3), 7.29-7.53(3H,m), 7.69(1H,d,J=7.3)].

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. additionwas added
  4. washthe mixture was washed with brine (50 ml) twice
  5. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  8. customrecrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-6d0af137a7f84df0be8ba3da7337a88d
出典データセット
uspto-grants-2000_04
特許番号
US06048885

反応ノート

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