2,6-Dichloroaniline → N-(2,6-Dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide

HRID 394054

反応式

HRID 394054 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[C:3]=1[CH2:11][CH2:12][C:13]([OH:15])=O.C(Br)(=O)C(Br)=O.C(N(C(C)C)CC)(C)C.[Cl:31][C:32]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:33]=1[NH2:34]>C(Cl)Cl.CN(C=O)C>[Cl:31][C:32]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:33]=1[NH:34][C:13](=[O:15])[CH2:12][CH2:11][C:3]1[C:4]([Br:10])=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[Br:1]

参加物

7

反応物 4

HCID 118462,6-DichloroanilineHCID 81531DiisopropylethylamineHCID 84841Ethanedioyl dibromideHCID 226479593-(2,6-Dibromo-4-methoxyphenyl)-propionic acid

生成物 1

HCID 22647977N-(2,6-Dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a −78° C. solution of 11.56 g of 3-(2,6-dibromo-4-methoxyphenyl)-propionic acid in 300 mL of CH2Cl2 was added dropwise 17.1 mL of a 1.0M solution of oxalyl bromide, then 1.7 mL of DMF. The mixture was allowed to warm to room temperature. When gas evolution ceased, the mixture was recooled to −78° C. Diisopropyl ethylamine (7.14 mL) was added dropwise, then a solution of 5.54 g of 2,6-dichloroaniline in 10 mL of CH2Cl2 was added dropwise. The mixture was allowed to warm to room temperature, then stirred overnight at this temperature. The white precipitate was collected to yield the N-(2,6-Dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide as a white solid. The filtrate was concentrated and recrystallized from EtOH to yield an additional amount of N-(2,6-Dichlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)-propionamide as a white solid. Mass spectrum (ESI) 481.9 (M+1). 1H NMR (500 MHz, DMSO-d6): δ 9.89 (s, 1H); 7.53 (d, J=8.2 Hz, 2H); 7.34 (t, J=8.0 Hz, 1H); 7.27 (s, 2H); 3.77 (s, 3H); 3.16 (m, 2H); 2.53 (m, 2H).

後処理

  1. customwas recooled to −78° C
  2. temperatureto warm to room temperature
  3. customThe white precipitate was collected

出典と根拠

ORDレコード
ord-641e101d02784040b6e438987a73b48a
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

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