Dicyclohexylcarbodiimide → Pent-4-ynoic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester

HRID 12010

反応式

HRID 12010 の反応式
[C:1]([OH:7])(=[O:6])[C:2]#[C:3][CH2:4][CH3:5].C1(N=C=NC2CCCCC2)CCCCC1.O[N:24]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[N:25]1>C1COCC1>[O:30]=[C:29]1[N:24]([O:6][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[N:25]=[N:26][C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]1=2

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-one2 回HCID 3243792-Pentynoic acid

生成物 1

HCID 59336624Pent-4-ynoic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

Pentynoic acid (200 mg, 2.04 mmol) was dissolved in THF (4 mL). The solution was cooled in a brine-icewater bath. A solution of dicyclohexylcarbodiimide (421 mg, 2.04 mmol) in THF (2 mL) was added. 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one (333 mg, 2.04 mmol) was added after 5 minutes. The reaction mixture was stirred 1 h at −10° C. and then 2 h at room temperature. TLC indicated full conversion of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (eluent: ethyl acetate). Precipitated salts were filtered off. The filtrate was concentrated in vacuo and crystallized from hexane (4 mL). The crystals were filtered off and dried. Yield: 450 mg, 93%. RF=0.8 (ethyl acetate).

後処理

  1. temperatureThe solution was cooled in a brine-icewater bath
  2. custom2 h
  3. customat room temperature
  4. filtrationPrecipitated salts were filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customcrystallized from hexane (4 mL)
  7. filtrationThe crystals were filtered off
  8. customdried

出典と根拠

ORDレコード
ord-c1a6f8c1a01b4e9980cd4e74051819a9
出典データセット
uspto-grants-2010_06
特許番号
US07727713B2

関連ノート

読み込み中…