Hydrochloric Acid → N-(Butylcarbamoyl)-4-nitrothiophene-2-sulfonamide

HRID 236531Notes

Reaction equation

HRID 236531 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:9]([NH2:12])(=[O:11])=[O:10])[S:7][CH:8]=1)([O-:3])=[O:2].[CH2:13]([N:17]=[C:18]=[O:19])[CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[CH2:13]([NH:17][C:18]([NH:12][S:9]([C:6]1[S:7][CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:10])=[O:11])=[O:19])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 202157164-Nitro-2-thiophenesulfonamide

Product 1

HCID 20215715N-(Butylcarbamoyl)-4-nitrothiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred suspension of 10 g of 4-nitrothiophene-2-sulfonamide, 6 g of n-butyl isocyanate and 7 g of anhydrous potassium carbonate in 100 ml of acetone was heated to reflux for 3 hours. The resultant viscous mixture was poured into ice-water and the pH adjusted to 2 by the addition of concentrated hydrochloric acid. The resulting tarry precipitate thus obtained was extracted into methylene chloride, separated from the aqueous phase, dried over magnesium sulfate, filtered and concentrated in-vacuo. The residue which showed absorption peaks by NMR at 0.7 to 1.7 (multiplet), consistent for butyl and at 8.3 and 8.5, consistent for the thiophene ring was used without further purification in the following example.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customThe resulting tarry precipitate thus obtained
  4. extractionwas extracted into methylene chloride
  5. customseparated from the aqueous phase
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in-vacuo
  9. customabsorption peaks by NMR at 0.7 to 1.7 (multiplet)

Sources & evidence

ORD record
ord-f3d0107aab53459391b983eaefcbe252
Source dataset
uspto-grants-1987_02
Patent number
US04645529

Reaction notes

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