Sodium Hydroxide → N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-methyl-hydroxylamine

HRID 1752110ノート

反応式

HRID 1752110 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.Cl.[CH3:17][O:18][NH2:19].[OH-].[Na+]>O1CCOCC1.O>[CH2:13]([NH:12][C:4]1[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:7]=[C:2]([NH:19][O:18][CH3:17])[N:3]=1)[CH2:14][CH3:15]

参加物

6

反応物 3

HCID 14798Sodium Hydroxide2 回HCID 183046-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamineHCID 521874O-Methylhydroxylamine hydrochloride

生成物 1

HCID 57377801N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-methyl-hydroxylamine収率 90.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

A mixture of 6-chloro-N,N′-dipropyl-[1,3,5]triazine-2,4-diamine (XXXIV) (2.30 g, 10.01 mmol), O-methyl-hydroxylamine hydrochloride (1.67 g, 20.02 mmol) and NaOH (0.72 g, 18.00 mmol) in 1,4-dioxane (30 mL) and water (6 mL) was heated at 60° C. for 3 h. After this time, NaOH (0.72 g, 18.00 mmol) was added and the reaction mixture was heated for another 3 h. The volatiles were removed under reduced pressure. Saturated NaHCO3 solution (100 mL) was added to the residue, the mixture was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography using gradient elution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5) to yield 2.17 g (90%) of N-(4,6-bis-n-propylamino-[1,3,5]triazin-2-yl)-O-methyl-hydroxylamine (XLI). ESI-MS (m/z): 241 [M+H]+

後処理

  1. temperaturethe reaction mixture was heated for another 3 h
  2. customThe volatiles were removed under reduced pressure
  3. additionSaturated NaHCO3 solution (100 mL) was added to the residue
  4. extractionthe mixture was extracted with EtOAc (3×25 mL)
  5. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customthe crude product was purified by flash column chromatography
  9. washelution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)

出典と根拠

ORDレコード
ord-c0893d3eedb14df6af5f29de7f3fe1d4
出典データセット
uspto-grants-2015_10
特許番号
US09162992B2

反応ノート

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