4-Tert-Butylaniline → HCID 2111998、化合物

HRID 736372ノート

反応式

HRID 736372 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].CCN(C(C)C)C(C)C.[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:30][CH:31]=1)([CH3:24])([CH3:22])[CH3:23]

参加物

5

反応物 3

HCID 698614-Tert-ButylanilineHCID 801724-Cyanobenzoyl chlorideHCID 81531Diisopropylethylamine

生成物 1

HCID 2111998HCID 2111998、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-cyanobenzoyl chloride (2 g, 12.08 mmol), DIEA (7.3 mL, 42 mmol), and 4-tert-butylaniline (1.9 mL, 11.9 mmol) were stirred in tetrahydrofuran (50 mL) overnight at room temperature. The tetrahydrofuran was removed under reduced pressure and replaced with ethyl acetate. The ethyl acetate was washed with H2O and brine, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluant gradient from 8:2 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate) to afford the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.41 (s, 1H), 8.08-8.12 (m, 2H), 8.01-8.04 (m, 2H), 7.66-7.69 (m, 2H), 7.37-7.41 (m, 2H), 1.28 (s, 9H); MS (ESI+) m/z 279 (M+H)+.

後処理

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. washThe ethyl acetate was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluant gradient from 8:2 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-32e45f698db047d4b8425cb819d8b26a
出典データセット
uspto-grants-2009_09
特許番号
US07595332B2

反応ノート

読み込み中…