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

HRID 530047노트

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HRID 530047 반응식
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]

참가 물질

6

반응물 3

HCID 14798Sodium Hydroxide2회HCID 183046-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamineHCID 521874O-Methylhydroxylamine hydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

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-propylamino-[1,3,5]triazin-2-yl)-O-methyl-hydroxylamine (XLI). ESI-MS (m/z): 241 [M+H]+

후처리

  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)

출처 및 근거

ORD 기록
ord-26a0f52df841413993f35d281dbd071d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09351972B2

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