Triethylamine → 7-Allyl-6-methoxy-1,4-dihydrobenz[d][1,3]oxazin-2-one

HRID 494949노트

반응식

HRID 494949 반응식
[NH2:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]=[CH2:12])[C:7]([O:13][CH3:14])=[CH:6][C:3]=1[CH2:4][OH:5].Cl[C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.O.N>O1CCCC1.O>[CH2:10]([C:8]1[C:7]([O:13][CH3:14])=[CH:6][C:3]2[CH2:4][O:5][C:16](=[O:18])[NH:1][C:2]=2[CH:9]=1)[CH:11]=[CH2:12]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 12896473Azane;hydrateHCID 576828172-Amino-5-methoxy-4-(2-propenyl)benzylalcohol

생성물 1

HCID 576828047-Allyl-6-methoxy-1,4-dihydrobenz[d][1,3]oxazin-2-one수율 126.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

677 mg of 2-amino-5-methoxy-4-(2-propenyl)benzylalcohol was dissolved in 20 ml of tetrahydrofuran under nitrogen atmosphere. Thereafter, 0.52 g of triphosgene and 1.46 ml of triethylamine were added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, while cooling on ice, water and ammonia water were added to the reaction solution until foaming was terminated. The reaction solution was diluted with ethyl acetate and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) and then reprecipitated from ethyl acetate, so as to obtain 485 mg of the subject compound.

후처리

  1. temperaturewhile cooling on ice
  2. additionwere added to the reaction solution until foaming
  3. customwas terminated
  4. additionThe reaction solution was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  9. customreprecipitated from ethyl acetate

출처 및 근거

ORD 기록
ord-fef5dadcdca042ddac5384dd06508fa4
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538123B2

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