Trifluoroacetic acid → 7-methyl4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine

HRID 585444노트

반응식

HRID 585444 반응식
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:8][O:9][C:4]=2[CH:3]=1.FC(F)(F)C(O)=O.[N:25](OCCCC)=[O:26]>C(OCC)C>[CH3:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([N:25]=[O:26])[CH:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:8][O:9][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 10996Butyl nitriteHCID 109111697-methyl-3-phenyl-2H-1,4-benzoxazine

생성물 1

HCID 223363397-methyl4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine수율 97%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
5 °C

실험 절차

To a mixture of 7-methyl-3-phenyl-2H-1,4-benzoxazine (22.5 g, 99.87 mmol) in ethyl ether (300 mL) is added trifluoroacetic acid (7.7 mL, 99.87 mmol). The resulting solution is chilled to 5° C. in an ice bath and n-butyl nitrite (12.26 mL, 99.87 mmol) is added dropwise. The mixture is stirred for 1 h; solids formed during the reaction. The solids are collected by filtration and washed with ether. The filtrates are partitioned between ether and water and the organic layers are washed three times with water (500 mL), dried over magnesium sulfate, and concentrated to dryness. The combined solids gave 23.22 g (97%) of 7-methyl-4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine.

후처리

  1. customsolids formed during the reaction
  2. filtrationThe solids are collected by filtration
  3. washwashed with ether
  4. customThe filtrates are partitioned between ether and water
  5. washthe organic layers are washed three times with water (500 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-e61060f5f7d143e5bb1390955ac9f605
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06932961B1

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