Nitric Acid → 2,5-Dichloro-4-nitro-thiophene-3-carboxylic acid methylamide

HRID 1688084Notes

Reaction equation

HRID 1688084 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[C:8]([Cl:10])[S:7][C:6]=1[Cl:11])=[O:4].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[CH3:1][NH:2][C:3]([C:5]1[C:9]([N+:12]([O-:14])=[O:13])=[C:8]([Cl:10])[S:7][C:6]=1[Cl:11])=[O:4]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23434132n-Methyl-(2,5-dichlorothiophen-3-yl)carboxamide

Product 1

HCID 672643122,5-Dichloro-4-nitro-thiophene-3-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

An ice-cold mixture of 2,5-dichloro-thiophene-3-carboxylic acid methylamide (475 mg) in H2SO4 (20 mL, 95-98%) was treated with fuming HNO3 (25 mL). The mixture was stirred for 1 hour and slowly poured onto ice, extracted with ethyl acetate three times, and dried over sodium sulfate. Filtration and concentration provided 2,5-dichloro-4-nitro-thiophene-3-carboxylic acid methylamide (565 mg): 1H NMR (300 MHz, CDCl3) δ 6.0 (bs, 1H), 3.0 (d, 3H).

Workup

  1. additionslowly poured onto ice
  2. extractionextracted with ethyl acetate three times
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-69ac62f4083d480d9dda50cbbee2f074
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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