4-Chloroaniline → 4'-Chloro-3-hydroxy-2-nitrobenzanilide

HRID 506535ノート

反応式

HRID 506535 の反応式
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([OH:1])[C:3]=2[N+:11]([O-:13])=[O:12])=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 78124-ChloroanilineHCID 757711-HydroxybenzotriazoleHCID 2932913-Hydroxy-2-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 178569794'-Chloro-3-hydroxy-2-nitrobenzanilide収率 92.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Hydroxy-2-nitrobenzoic acid (2.00 g) was dissolved in 110 ml of N,N-dimethylformamide, then 1.53 g of 4-chloroaniline, 3.15 g of 1-ethyl-3-[3-(N,N-dimethylamino)propyl]carbodiimide hydrochloride and 2.21 g of 1-hydroxybenzotriazole were added thereto and the mixture was stirred at room temperature for 4 days. The reaction solution was concentrated in vacuo, a saturated saline was added to the concentrate and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by means of a silica gel column chromatography using chloroform:methanol (100:1) as an eluate to give 2.97 g of 4′-chloro-3-hydroxy-2-nitrobenzanilide.

後処理

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additiona saturated saline was added to the
  3. concentrationconcentrate
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by means of a silica gel column chromatography

出典と根拠

ORDレコード
ord-154e57eab38c4b56926fa2af636d2b5c
出典データセット
uspto-grants-2010_08
特許番号
US07786106B2

反応ノート

読み込み中…