Methyl iodide → 2-methyl-5-(4-nitrophenyl)-2H-tetrazole

HRID 1921792ノート

反応式

HRID 1921792 の反応式
[H-].[Na+].[CH3:3]I.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[CH:10][CH:9]=1)([O-:7])=[O:6]>CN(C=O)C>[CH3:3][N:16]1[N:17]=[N:18][C:14]([C:11]2[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=2)=[N:15]1.[CH3:3][N:15]1[C:14]([C:11]2[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=2)=[N:18][N:17]=[N:16]1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526570HCID 178526570、化合物

生成物 2

HCID 3231922-methyl-5-(4-nitrophenyl)-2H-tetrazole収率 49%HCID 126725461-Methyl-5-(4-nitrophenyl)-1H-tetrazole収率 7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
5 °C

実験手順

To a stirred solution of 60% NaH (0.116 g, 2.89 mmol) and MeI (0.196 mL, 3.15 mmol) in DMF (2 mL) (cooled to 0° C., under N2) is added dropwise, a solution of 5-(4-nitrophenyl)-1H-tetrazole (0.502, 2.63 mmol) in DMF (7 mL). The reaction mixture is stirred under N2 for 1 hour and 30 min at 5° C. and then quenched with water and extracted with EtOAc. The organic layers are combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated to give a residue purified by silica gel column chromatography. Elution with 80:20 followed by 60:40 petroleum ether-EtOAc affords 2-methyl-5-(4-nitro-phenyl)-2H-tetrazole (0.265 g, 49%) as a white solid and 1-methyl-5-(4-nitro-phenyl)-1H-tetrazole (37.7 mg, 7%) as a yellow solid. The isomers are identified by NOE experiments.

後処理

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. washwashed with sat. NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue
  8. custompurified by silica gel column chromatography
  9. washElution with 80:20

出典と根拠

ORDレコード
ord-859b12e4195442b184994c3148c6da63
出典データセット
uspto-grants-2012_05
特許番号
US08173656B2

反応ノート

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