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

HRID 257600

Reaction equation

HRID 257600 reaction equation
[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

Participants

6

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-163f67be382447bcb75b33046858f377
Source dataset
uspto-grants-1993_11
Patent number
US05262539

Linked notes

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