Triethylamine → 2,6-Dinitro-N-ethoxy-p-toluidine

HRID 371688ノート

反応式

HRID 371688 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1Cl)([O-:3])=[O:2].Cl.[CH2:16]([O:18][NH2:19])[CH3:17].C(N(CC)CC)C>CO>[N+:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[NH:19][O:18][CH2:16][CH3:17])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 76850O-ethylhydroxylamine hydrochloride2 回HCID 789184-Chloro-3,5-dinitrotoluene

生成物 1

HCID 213298902,6-Dinitro-N-ethoxy-p-toluidine収率 70%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A suspension of 10.0 g. (0.046 mole) of 2,6-dinitro-4-methylchlorobenzene in 100 ml. of methanol was prepared, and to the suspension there was added 7.6 g. (0.092 mole) of ethoxyamine hydrochloride, and 13.9 g. (0.138 mole) of triethylamine. The reaction mixture was stirred for about 30 minutes at room temperature and then heated and stirred for about 30 minutes at about 50° C., after which an additional 16.7 g. (0.20 mole) of ethoxyamine hydrochloride was added, and the reaction mixture was stirred and refluxed for about 24 hours. An NMR spectrum of the reaction mixture indicated the presence of the desired product in about 70 percent yield. The reaction product mixture was poured over a mixture of ice and water, and the aqueous mixture filtered. The solid obtained was recrystallized from petroleum ether (b.p. 60°-71° C.) to yield 5.5 g. of product having a melting point of about 64°-66° C. The product was identified by its NMR spectrum as 2,6-dinitro-N-ethoxy-p-toluidine.

後処理

  1. additionA suspension of 10.0 g
  2. additionto the suspension there was added 7.6 g
  3. temperatureheated
  4. stirringstirred for about 30 minutes at about 50° C.
  5. stirringthe reaction mixture was stirred
  6. temperaturerefluxed for about 24 hours

出典と根拠

ORDレコード
ord-05c39ee319054ac28e4d4754532e923a
出典データセット
uspto-grants-1978_05
特許番号
US04087460

反応ノート

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