Hydrochloric Acid → N-phenyl-5-nitro-2-thienylamine

HRID 257600

反応式

HRID 257600 の反応式
[N+:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)([O-:3])=[O:2].[C:9]1([NH:15]SC2C=CC=CC=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CN(C)C=O>[C:9]1([NH:15][C:6]2[S:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:8][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:9]1([NH:15][C:8]2[CH:7]=[CH:6][S:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 11866Thiophene, 2-nitro-HCID 315504Benzenesulfenamide, N-phenyl-

生成物 2

HCID 13039998N-phenyl-2-nitro-3-thienylamine収率 15%HCID 19783600N-phenyl-5-nitro-2-thienylamine収率 42%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

2.9 g of 2-nitrothiophene and 4 g of N-phenylbenzenesulphenamide, dissolved in 10 ml of dimethylformamide, are added dropwise to a stirred solution of 6 g of potassium tert.-butylate in 60 ml of dimethylformamide, while the temperature is kept at about -20° C. The mixture is stirred for a further 15 minutes; then an excess of dilute hydrochloric acid is added to the mixture, after which it is treated in the same way as described in Example 1. The crude product is separated by column chromatography; N-phenyl-5-nitro-2-thienylamine (melting point 186° C., yield 1.8 g, 42%) and N-phenyl-2-nitro-3-thienylamine (melting point 105° C., yield 0.7 g, 15%) are obtained.

後処理

  1. customis kept at about -20° C
  2. additionafter which it is treated in the same way
  3. customThe crude product is separated by column chromatography

出典と根拠

ORDレコード
ord-163f67be382447bcb75b33046858f377
出典データセット
uspto-grants-1993_11
特許番号
US05262539

関連ノート

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