Hydrochloric Acid → 5-Chloro-N1-(4'-cyanophenyl)-2,4-dinitroaniline

HRID 1876450

反応式

HRID 1876450 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)#[N:16].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH:7]=1)[NH:21][C:20]1[CH:22]=[CH:23][C:17]([C:15]#[N:16])=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 133964-AminobenzonitrileHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 706973965-Chloro-N1-(4'-cyanophenyl)-2,4-dinitroaniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2,4-Dichloro-1,5-dinitrobenzene (II-1, 1.2 g, 5 mmol) and p-cyanoaniline (III-1, 0.59 g, 5 mmol) were dissolved in N,N-dimethylformamide (DFM, 10 ml). To the solution was added potassium tert-butoxide (1.4 g, 12.5 mmol) in batches in ice water bath. The mixture was allowed to react at room temperature for 45 minutes. The reaction liquid was poured into ice water. The pH value was adjusted to about 6 with dilute hydrochloric acid. The mixture was stirred for 30 minutes to precipitate a solid. The solid was filtered, washed with water to neutrality, dried, and separated on silica gel column (eluted with ethyl acetate: petroleum ether) to obtain a compound VI-1 (1.44 g, faint yellow solid). 1H NMR (CDCl3) δ ppm 7.41 (1H, s, ArH-6), 7.57 (2H, d, J=8.7 Hz, ArH-3′, 5′), 7.91 (2H, d, J=8.7 Hz, ArH-2′, 6′), 8.90 (1H, s, ArH-3), 10.07 (1H, s, NH).

後処理

  1. customto react at room temperature for 45 minutes
  2. customThe reaction liquid
  3. customto precipitate a solid
  4. filtrationThe solid was filtered
  5. washwashed with water to neutrality
  6. customdried
  7. customseparated on silica gel column (eluted with ethyl acetate: petroleum ether)
  8. customto obtain a compound VI-1 (1.44 g, faint yellow solid)

出典と根拠

ORDレコード
ord-3438de63c1f34272bac3be02e2cce82c
出典データセット
uspto-grants-2012_11
特許番号
US08309602B2

関連ノート

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