Imidazole → 2-Chloro-4-(1-imidazolyl)-6-dimethylamino-1,3,5-triazine

HRID 2395617노트

반응식

HRID 2395617 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]([CH3:11])[CH3:10])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[N:5]=[C:4]([N:9]([CH3:11])[CH3:10])[N:3]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 169852,4-Dichloro-6-(dimethylamino)-1,3,5-triazine

생성물 1

HCID 105133592-Chloro-4-(1-imidazolyl)-6-dimethylamino-1,3,5-triazine수율 38,860.398%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Cyanuric chloride (11.0 g, 59.6 mmol) was dissolved in ethylene glycol dimethyl ether (100 ml), cooled to -5° C. and gradually added dropwise with 50% aqueous dimethylamine solution (10.8 ml, 120 mmol). This reaction mixture was stirred at the same temperature for 2 hours and then stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure. The obtained residue was added with dichloromethane and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed to obtain 11.0 g (yield: 95.4%) of 2,4-dichloro-6-dimethylamino-1,3,5-triazine as colorless crystals having melting point of 122.5° C.-123° C. (2) The obtained 2,4-dichloro-6-dimethylamino-1,3,5-triazine (1.93 g, 10.0 mmol) was dissolved in DMF (8 ml), added with anhydrous potassium carbonate (1.40 g, 10.1 mmol) and cooled to -5° C.-0° C. This mixture was gradually added with imidazole (695 mg, 10.2 mmol). The reaction mixture was stirred at room temperature overnight and evaporated under reduced pressure. The residue was added with ethyl acetate and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water, dried over anhydrous magnesium sulfate and evaporated. The obtained residue was purified by silica gel column chromatography, using ethyl acetate and methanol (95:5) as eluant, to obtain 873 g (yield: 38.8%) of 2-chloro-4-(1-imidazolyl)-6-dimethylamino-1,3,5-triazine as colorless crystals having melting point of 88° C.-92° C.

후처리

  1. temperaturecooled to -5° C.-0° C
  2. customevaporated under reduced pressure
  3. additionThe residue was added with ethyl acetate and water
  4. stirringshaken
  5. additionfor mixing
  6. customThe organic layer was separated from the mixture
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-abbc7050e5114c3b89809bd32464dcbf
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05489591

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