Ammonium Hydroxide → HCID 67219804, compound

HRID 900876Notes

Reaction equation

HRID 900876 reaction equation
[CH3:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[OH-].[NH4+:15]>C1COCC1>[CH3:1][C:2]1[S:6][C:5]([S:7]([NH2:15])(=[O:9])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 214989645-Methyl-4-nitrothiophene-2-sulfonyl chloride

Product 1

HCID 67219804HCID 67219804, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-methyl-4-nitrothiophene-2-sulfonyl chloride [CAS No. 61714-77-0] (1.0 g, 4.14 mmol) in THF (20 ml) was added at 0° C. (ice water bath) ammonium hydroxide solution (25%, 5 ml). The reaction mixture was stirred at room temperature for 1 h, evaporated, poured into water (30 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (2×30 ml), dried (MgSO4) and evaporated. The crude product was further purified by crystallization from ethyl acetate/hexane to yield 5-methyl-4-nitro-thiophene-2-sulfonamide (0.75 g, 82%) as a brown solid. MS (ISP) 221.0 [(M−H)−], mp 120° C.

Workup

  1. customevaporated
  2. additionpoured into water (30 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organic layers were washed with brine (2×30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was further purified by crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-069a2ee9b8ae4ad6b600927f921ef115
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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