Triethylamine → Methyl 4-[3-(1-adamantyl)-4-methoxyphenylureido]benzoate

HRID 235311ノート

反応式

HRID 235311 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8](C(O)=O)=[CH:7][CH:6]=1)=[O:4].C([N:16]([CH2:19]C)CC)C.ClC(OCC)=[O:23].[N-]=[N+]=[N-].[Na+].[C:31]12([C:41]3[CH:42]=[C:43]([CH:45]=[CH:46][C:47]=3[O:48][CH3:49])[NH2:44])[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]3)[CH2:32]1)[CH2:38]2>O1CCCC1.O>[C:31]12([C:41]3[CH:42]=[C:43]([NH:44][C:19](=[O:23])[NH:16][C:8]4[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=4)[CH:45]=[CH:46][C:47]=3[O:48][CH3:49])[CH2:38][CH:37]3[CH2:39][CH:33]([CH2:34][CH:35]([CH2:36]3)[CH2:40]1)[CH2:32]2

参加物

8

反応物 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 15513Monomethyl terephthalateHCID 33557Sodium AzideHCID 80271163-(1-Adamantyl)-4-methoxyaniline

生成物 1

HCID 67714159Methyl 4-[3-(1-adamantyl)-4-methoxyphenylureido]benzoate収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 2.81 g (15.6 mmol) of 4-(methoxycarbonyl)benzoic acid in 30 ml of tetrahydrofuran is placed at 0° C., then treated with 2.61 ml (18.7 mmol) of triethylamine and 1.94 ml (20.3 mmol) of ethyl chloroformate and left stirring for 1 hour at 0° C. A solution of 1.52 g (23.4 mmol) of sodium azide in 10 ml of water is added to this medium, the mixture is left stirring at 0° C. for 3 hours and the reaction medium is then poured into ice-cold water and extracted with ethyl ether. The organic phase is washed with water, dried over magnesium sulphate and evaporated. The residue is dissolved in 30 ml of toluene, heated to 100° C. for 1.5 hours and then cooled to room temperature. 4.82 g (18.7 mmol) of 3-(1-adamantyl)-4-methoxyaniline are then added dropwise to the foregoing solution and the mixture is stirred at 50° C. for 1.5 hours. It is evaporated to dryness, the solid is taken up with ethyl ether and the organic phase is dried over magnesium sulphate and evaporated. The residue is recrystallized in ethyl acetate to yield 6.16 g (91%) of methyl 4-[3-(1-adamantyl)-4-methoxyphenylureido]benzoate, melting point 223°-224° C.

後処理

  1. customis placed at 0° C.
  2. waitleft
  3. waitthe mixture is left
  4. stirringstirring at 0° C. for 3 hours
  5. additionthe reaction medium is then poured into ice-cold water
  6. extractionextracted with ethyl ether
  7. washThe organic phase is washed with water
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. dissolutionThe residue is dissolved in 30 ml of toluene
  11. temperatureheated to 100° C. for 1.5 hours
  12. temperaturecooled to room temperature
  13. stirringthe mixture is stirred at 50° C. for 1.5 hours
  14. customIt is evaporated to dryness
  15. dry with materialthe organic phase is dried over magnesium sulphate
  16. customevaporated
  17. customThe residue is recrystallized in ethyl acetate

出典と根拠

ORDレコード
ord-c38b757ce10e4c648e584a104b718794
出典データセット
uspto-grants-1997_01
特許番号
US05597839

反応ノート

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