Acetic Acid → HCID 178510324, 화합물

HRID 2213771

반응식

HRID 2213771 반응식
[C:1](#[N:3])[CH3:2].C([Li])CCC.C(O[C:12]([C:14]1[O:15][C:16]2[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=2[C:18]=1[N:19]=[CH:20]N(C)C)=[O:13])C.C(O)(=O)C>O1CCCC1>[OH:13][C:12]1[C:2]([C:1]#[N:3])=[CH:20][N:19]=[C:18]2[C:17]3[CH:24]=[CH:25][CH:26]=[CH:27][C:16]=3[O:15][C:14]=12

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 98349623-(Dimethylaminomethyleneamino)benzofuran-2-carboxylic Acid Ethyl EsterHCID 178418339Butyllithium

생성물 1

HCID 178510324HCID 178510324, 화합물수율 82.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

A solution of 1.5 mL (30.0 mmol) of acetonitrile in 30 mL of tetrahydrofuran is added to a −78° C. solution of 11.4 mL of 2.5 M n-butyllithium (29.00 mmol) in 35 mL of tetrahydrofuran. After stirring at −78° C. for 15 min a solution of 3.7 g (14.2 mmol) of 3-(dimethylaminomethyleneamino)benzofuran-2-carboxylic acid ethyl ester in 50 mL of tetrahydrofuran is added dropwise. After stirring at −78° C. for 30 minutes, the reaction mixture is allowed to warm to 0° C. The reaction mixture is cooled to −78° C. and 3 mL of acetic acid is added. The solution is warmed to room temperature and the resulting precipitate is collected. This solid is combined with 20 mL of acetic acid and heated at reflux temperature for 1.5 hours. The mixture is cooled to room temperature and the solid is collected by filtration washing with saturated sodium bicarbonate, water, diethyl ether and ethyl acetate to provide 2.45 g of a red solid, mp>310° C.

후처리

  1. additionis added dropwise
  2. temperatureto warm to 0° C
  3. temperatureThe reaction mixture is cooled to −78° C.
  4. temperatureThe solution is warmed to room temperature
  5. customthe resulting precipitate is collected
  6. temperatureheated
  7. temperatureat reflux temperature for 1.5 hours
  8. temperatureThe mixture is cooled to room temperature
  9. filtrationthe solid is collected by filtration
  10. washwashing with saturated sodium bicarbonate, water, diethyl ether and ethyl acetate

출처 및 근거

ORD 기록
ord-c74197ad13054691ab127fae24ce4a95
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105531B2

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