Acetic Acid → HCID 178510324、化合物

HRID 2213771

反応式

HRID 2213771 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 178510324HCID 178510324、化合物収率 82.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c74197ad13054691ab127fae24ce4a95
出典データセット
uspto-grants-2006_09
特許番号
US07105531B2

関連ノート

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