Ammonia → (R)-5-(3-Bromo-6-nitro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

HRID 81559

반응식

HRID 81559 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C@@:11]2([CH3:18])[NH:16][C:15](=S)[CH2:14][O:13][CH2:12]2)[CH:5]=[C:6]([N+]([O-])=O)[CH:7]=1.C([O:23]O)(C)(C)C.[OH-:25].[NH3:26].[O-]S([O-])(=S)=O.[Na+].[Na+].[NH3:34]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C@:11]2([CH3:18])[CH2:12][O:13][CH2:14][C:15]([NH2:16])=[N:34]2)[C:5]([N+:26]([O-:23])=[O:25])=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 222AmmoniaHCID 6410tert-Butyl hydroperoxideHCID 24477Sodium ThiosulfateHCID 21862953Ammonia hydroxideHCID 86667520HCID 86667520, 화합물

생성물 1

HCID 86716531(R)-5-(3-Bromo-6-nitro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholine-3-thione (2.86 g, 7.77 mmol) was dissolved in 7M NH3 in methanol (50 ml). Tert-Butylhydroperoxide (9.41 ml, 78 mmol) and ammonia hydroxide (25% sol., 21.2 ml, 136 mmol) were added and the reaction was stirred at r.t. for 2 hrs. Upon completion, 50 ml half-saturated Na2S2O3 solution was added to the reaction and the product was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure, yielding the title compound as yellowish solid. 1H-NMR (360 MHz, DMSO-d6): 8.34 (s, 1H), 8.25 (s, 1H), 8.12 (s, 1H), 5.85 (br, 2H), 4.01 (m, 1H), 3.80 (m, 1H), 3.55 (m, 1H), 1.38 (s, 3H); MS: 314 [(M+H)+].

후처리

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customVolatiles were removed under reduced pressure

출처 및 근거

ORD 기록
ord-adb68345b7214d86b2eae8950c5ec4b1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846658B2

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