2-Naphthylamine → 3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide

HRID 888567

反応式

HRID 888567 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.C1C=CC2C=[C:25]([NH2:30])C=CC=2C=1.Cl.CN(C)CCCC(N=C=N)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10]([NH:30][CH3:25])=[O:11])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 70572-NaphthylamineHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochlorideHCID 576913963-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid

生成物 1

HCID 593319703-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-(4-bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid (0.25 g, 0.74 mmol) and 1-hydroxybenatriazole (0.12 g, 0.88 mmol) in dichloromethane (3 ml) was stirred for 15 minutes before addition of napthylamine (40% solution in water, 0.11 μl, 1.47 mmol) and 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (0.17 g, 0.88 mmol). The reaction mixture was stirred for 16 hours, solvent removed under reduced pressure and the residue partitioned between ethyl acetate and 1N HCl. The organic layer was separated, washed with saturated sodium hydrogen carbonate, brine, dried (MgSO4), filtered and concentrated to yield the title compound which was used in the next step without further purification. LC/MS: (PS-A2) Rt 3.20 [M+H]+ 353.95.

後処理

  1. customsolvent removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and 1N HCl
  3. customThe organic layer was separated
  4. washwashed with saturated sodium hydrogen carbonate, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f1a9e204f11d4b1ca2f4c7bf63151e25
出典データセット
uspto-grants-2012_08
特許番号
US08247576B2

関連ノート

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