Pyridine → 2,2,2-Trichloroethyl {6-[acetyl(methyl)amino]pyridin-3-yl}carbamate

HRID 2263081ノート

反応式

HRID 2263081 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.N1C=CC=CC=1.Cl[C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21]>O1CCCC1>[C:9]([N:8]([CH3:12])[C:5]1[N:6]=[CH:7][C:2]([NH:1][C:20](=[O:21])[O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 59301435N-(5-aminopyridin-2-yl)-N-methylacetamide

生成物 1

HCID 866254922,2,2-Trichloroethyl {6-[acetyl(methyl)amino]pyridin-3-yl}carbamate収率 52.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-(5-aminopyridin-2-yl)-N-methylacetamide (1.00 g, 6.06 mmol) and pyridine (1.47 ml, 18.2 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.25 ml, 9.09 mmol) with ice-cooling, the mixture was stirred for 0.5 hour with ice-cooling, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to obtain the desired product (1.08 g, 52.4%) as a solid.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-d5f1869f2f9c408995a5b1d87642dedb
出典データセット
uspto-grants-2010_12
特許番号
US07851473B2

反応ノート

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