Ammonia → 5-Aminothiophene-2-sulfonamide

HRID 1182067Notes

Reaction equation

HRID 1182067 reaction equation
[N+:1](C1C=C(S(Cl)(=O)=O)SC=1)([O-])=O.[N+:13]([C:16]1[S:20][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:18][CH:17]=1)([O-])=O.N>CC(C)=O>[NH2:13][C:16]1[S:20][C:19]([S:21]([NH2:1])(=[O:23])=[O:22])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 179863784-Nitrothiophene-2-sulfonyl chlorideHCID 217873475-Nitrothiophene-2-sulfonyl chloride

Product 1

HCID 247115985-Aminothiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 11.3 g (49.6 mmol) of a mixture that consists of 4-nitro-thiophene-2-sulfonyl chloride and 5-nitro-thiophene-2-sulfonyl chloride (ratio: 1.4/1.0) in acetone is added while being stirred to a saturated solution of ammonia in 170 ml of acetone at −35° C. After 30 minutes, the batch is filtered and concentrated by evaporation. The crude product is dissolved without further purification in 100 ml of ethanol. It is mixed with 6 g of Raney nickel and hydrogenated for 8 hours under low pressure at room temperature. The batch is filtered and concentrated by evaporation. 11.7 g of a mixture that consists of 4-amino-thiophene-2-sulfonic acid amide and 5-amino-thiophene-2-sulfonic acid amide is obtained at a ratio of 2:1, which is used without further purification.

Workup

  1. additionis added
  2. filtrationthe batch is filtered
  3. concentrationconcentrated by evaporation
  4. dissolutionThe crude product is dissolved without further purification in 100 ml of ethanol
  5. additionIt is mixed with 6 g of Raney nickel
  6. waithydrogenated for 8 hours under low pressure at room temperature
  7. filtrationThe batch is filtered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2f4328d4c34847f0acd612a6f9c1073a
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Reaction notes

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