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

HRID 257600

반응식

HRID 257600 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-163f67be382447bcb75b33046858f377
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262539

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