Sodium Hydroxide → 3,3'-Dichlorobenzidine

HRID 465159

反応式

HRID 465159 の反応式
ClC1C=CC=CC=1[N+:8](=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])[O-:9].[OH-:18].[Na+].O.NN>CO.[Ni].O>[Cl:17][C:12]1[CH:13]=[C:14]([C:14]2[CH:15]=[CH:16][C:11]([NH2:10])=[C:12]([Cl:17])[CH:13]=2)[CH:15]=[CH:16][C:11]=1[NH2:10].[N:8]([OH:9])=[O:18]

参加物

8

反応物 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 83576Diazene, 1,2-bis(2-chlorophenyl)-, 1-oxide

生成物 2

HCID 70703,3'-DichlorobenzidineHCID 24529Nitrous Acid

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

53.4 g of 2,2'-dichloroazoxybenzene are stirred in 60 ml of methanol. 0.6 g of sodium hydroxide and 11.8 ml of hydrazine hydrate are added and the mixture is warmed to 65° C. After Raney nickel has been added (a total of about 0.05 g in 2-3 portions) vigorous evolution of nitrogen starts. The reduction has ended after 30 minutes. The mixture is cooled to 10° C. and diluted with water and the 2,2'-dichlorohydrazobenzene which has crystallised out is filtered off and washed with water until neutral. After the rearrangement to 3,3'-dichlorobenzidine and tetrazotisation with nitrous acid, a yield of 86% of theory is obtained.

後処理

  1. temperatureThe mixture is cooled to 10° C.
  2. customthe 2,2'-dichlorohydrazobenzene which has crystallised out
  3. filtrationis filtered off
  4. washwashed with water until neutral

出典と根拠

ORDレコード
ord-a4b05ef6fb064d9e9cdad462c02b34a0
出典データセット
uspto-grants-1985_10
特許番号
US04550207

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