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

HRID 865886노트

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HRID 865886 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6f39ba0f4878416a9d12ff9aa7294408
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05567721

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