4-Nitroaniline → 4,4'-Dinitrocarbanilide

HRID 648072

反応式

HRID 648072 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])OC)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([O-:17])=[O:16]>C1(C)C(C)=CC=CC=1>[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[O:14])=[CH:20][CH:19]=1)([O-:17])=[O:16]

参加物

4

反応物 2

HCID 74754-NitroanilineHCID 74752Carbamic acid, N-(4-nitrophenyl)-, methyl ester

生成物 1

HCID 95094,4'-Dinitrocarbanilide収率 85.2%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

9.81 g (50 mmoles) of methyl N-(4-nitrophenyl)carbamate, 6.9 g (50 mmoles) of 4-nitroaniline, 140 ml of xylene and 11.8 g (about 50 mmoles) of Genamin CS 302 D (a mixture of N,N-dimethyl-C10-18 alkylamines sold by the firm Hoechst AG) are introduced into a flask equipped with a reflux condenser, and the mixture is boiled. The yellow crystals of the end-product appear already in the 3rd minute of boiling, and the amount of the crystalline precipitate rapidly increases. After 0.5 hours of boiling the thick, orange crystal suspension is filtered in vacuo when hot, the filter cake is washed twich with 20 ml of hot xylene, each, and then with acetone, finally the product is dried in vacuo. 12.78 g (85.2%) of N,N'-bis(4-nitrophenyl)-urea are obtained. The product is uniform when examined by layer chromatography utilizing a 3:1 mixture of n-hexane and acetone as solvent, and the chromatographic appearance of the product is identical with that of the authentic sample.

後処理

  1. additionare introduced into a flask
  2. customequipped with a reflux condenser
  3. temperaturethe amount of the crystalline precipitate rapidly increases
  4. filtrationthe thick, orange crystal suspension is filtered in vacuo when hot
  5. washthe filter cake is washed twich with 20 ml of hot xylene
  6. dry with materialeach, and then with acetone, finally the product is dried in vacuo

出典と根拠

ORDレコード
ord-aed9e56292a64419a6460ebcc29a40e1
出典データセット
uspto-grants-1983_10
特許番号
US04410697

関連ノート

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