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

HRID 1425669

反応式

HRID 1425669 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-b4512c63238b41e6808a75cbeb137263
出典データセット
uspto-grants-2015_01
特許番号
US08932992B2

関連ノート

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