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

HRID 1279705ノート

反応式

HRID 1279705 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
5 °C

実験手順

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-methyl4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine.

後処理

  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

出典と根拠

ORDレコード
ord-905ccb680cf14deaa9383bbfbcd27cdd
出典データセット
uspto-grants-2002_09
特許番号
US06448397B1

反応ノート

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