Triethylamine → 3-Iodo-4-methyl-N-[3-(4-morpholinyl)phenyl]benzamide

HRID 31402

反応式

HRID 31402 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].C(N(CC)CC)C.[N:19]1([C:25]2[CH:26]=[C:27]([NH2:31])[CH:28]=[CH:29][CH:30]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:26]=1)=[O:6]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 8477683-(Morpholin-4-yl)aniline2 回HCID 177521573-Iodo-4-methylbenzoyl chloride2 回

生成物 1

HCID 445802833-Iodo-4-methyl-N-[3-(4-morpholinyl)phenyl]benzamide収率 67.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

3-Iodo4-methylbenzoyl chloride (Intermediate 1) (19.5 g, 69.6 mmol) was added portion-wise to a mixture of triethylamine (48 ml, 350 mmol) and 3-(4-morpholinyl)benzenamine (Intermediate 3) (12.6 g, 70.6 mmol) in dimethyl formamide (150 ml) and the mixture was heated at 80° C. for 16 hours. The solvent was removed in vacuo and the residue taken up in chloroform (200 ml). The organic layer was washed with water (2×100 ml), 2M sodium hydroxide solution (100 ml) and brine (100 ml), dried over magnesium sulfate, filtered and solvent removed in vacuo. The resulting yellow solid was titurated with diethyl ether and collected by filtration to yield the desired product as an off-white solid (20.0 g, 47.0 mmol). The product was used in subsequent reactions without further purification.

後処理

  1. customThe solvent was removed in vacuo
  2. washThe organic layer was washed with water (2×100 ml), 2M sodium hydroxide solution (100 ml) and brine (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-a5cf4389c1a341c39cbf2e801622dc5c
出典データセット
uspto-grants-2008_09
特許番号
US07425555B2

関連ノート

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