Dipropylamine → Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

HRID 13992

反応式

HRID 13992 の反応式
C(C1NC=CN=1)(C1NC=CN=1)=O.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:22]=1)[C:17]([OH:19])=O.[CH2:27]([NH:30][CH2:31][CH2:32][CH3:33])[CH2:28][CH3:29]>C1COCC1>[Br:13][C:14]1[CH:22]=[C:21]([CH:20]=[C:16]([C:17]([N:30]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:28][CH3:29])=[O:19])[CH:15]=1)[C:23]([O:25][CH3:26])=[O:24]

参加物

5

反応物 3

HCID 8902DipropylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

生成物 1

HCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Carbonyl diimidazole (3.0 g, 18 mmol) is added to a solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (XIX, PREPARATION 2, 3.9 g, 15 mmol) in THF (30 mL). The mixture is stirred for 0.5 hours. Dipropylamine (AMINE, 4.2 mL, 30 mmol) is added to the mixture, which is then stirred for 24 hours. The solvent is then removed under reduced pressure and the mixture is partitioned between ethyl acetate and water. The organic phase is then washed with saline, dried over anhydrous magnesium sulfate, filtered, and concentrated. Column chromatography (silica gel; ethyl acetate/hexanes, 15/85) gives the title compound, IR (diffuse reflectance) 2968, 2958, 1714, 1637, 1479, 1440, 1422, 1321, 1310, 1288, 1273, 1252, 889, 772 and 718 cm−1; NMR (300 MHz, CDCl3) δ 8.21, 7.96, 7.70, 3.95, 3.46, 3.15, 1.69, 1.57, 1.00 and 0.78; MS (ESI+) for C15H20BrNO3 m/z (M+H)+=344.1.

後処理

  1. stirringis then stirred for 24 hours
  2. customThe solvent is then removed under reduced pressure
  3. customthe mixture is partitioned between ethyl acetate and water
  4. washThe organic phase is then washed with saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-629d80db91774f4996754a649f0d3600
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

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