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

HRID 1921792노트

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HRID 1921792 반응식
[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

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526570HCID 178526570, 화합물

생성물 2

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-859b12e4195442b184994c3148c6da63
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173656B2

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