Trifluoroacetic acid → 3-(1-adamantyl)4-methoxy-N-(trifluoroacetyl)aniline

HRID 865885ノート

反応式

HRID 865885 の反応式
C([N:3](CC)CC)C.ClC(OCC)=O.[C:14]12([C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=3[O:33][CH3:34])C(O)=O)[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.[N-]=[N+]=[N-].[Na+].[F:39][C:40]([F:45])([F:44])[C:41](O)=[O:42].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[C:14]12([C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=3[O:33][CH3:34])[NH:3][C:41](=[O:42])[C:40]([F:45])([F:44])[F:39])[CH2:21][CH:20]3[CH2:22][CH:16]([CH2:17][CH:18]([CH2:19]3)[CH2:23]1)[CH2:15]2

参加物

9

反応物 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid

生成物 1

HCID 190682803-(1-adamantyl)4-methoxy-N-(trifluoroacetyl)aniline収率 57%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

11.70 ml (84 mmol) of triethylamine in 10 ml of tetrahydrofuran and 8.70 ml (91 mmol) of ethyl chloroformate in 10 ml of tetrahydrofuran are successively added dropwise to a solution of 20.6 g (70 mmol) of 3-(1-adamantyl)-4-methoxybenzoic acid in 200 ml of tetrahydrofuran at 0° C. The reaction medium is stirred for 40 minutes at 0° C., 6.83 g (105 mmol) of sodiumazide, dissolved in 30 ml of water, are then added to this medium and the mixture is left stirring at 0° C. for 2 hours. The reaction medium is poured into ice-cold water, the mixture is extracted with dichloromethane and the organic phase is washed with water, dried over magnesium sulphate and evaporated. The residue is dissolved in 400 ml of dichloromethane, 7.3 ml (0.094 mol) of trifluoroacetic acid are added and the mixture is heated to reflux for 30 hours. The reaction medium is poured into saturated sodium bicarbonate solution and the organic phase is dried over magnesium sulphate and evaporated. The residue is chromatographed on silica with a dichloromethane/hexane (30:70) mixture to yield 14.1 g (57%) of 3-(1-adamantyl)-4-methoxy-N-(trifluoroacetyl)aniline, melting point 166°-167° C.

後処理

  1. additionare then added to this medium
  2. waitthe mixture is left
  3. stirringstirring at 0° C. for 2 hours
  4. additionThe reaction medium is poured into ice-cold water
  5. extractionthe mixture is extracted with dichloromethane
  6. washthe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. dissolutionThe residue is dissolved in 400 ml of dichloromethane
  10. temperaturethe mixture is heated
  11. temperatureto reflux for 30 hours
  12. dry with materialthe organic phase is dried over magnesium sulphate
  13. customevaporated
  14. customThe residue is chromatographed on silica with a dichloromethane/hexane (30:70) mixture

出典と根拠

ORDレコード
ord-cb099912a386488f9549bbc5f04d7431
出典データセット
uspto-grants-1996_10
特許番号
US05567721

反応ノート

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