Hydrazine hydrate (1:1) → HCID 11807266, compound

HRID 1419734Notes

Reaction equation

HRID 1419734 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7](=[O:10])(=[O:9])[NH2:8])=[C:4]([C:11]([O:13]CC)=O)[CH:3]=1.O.[NH2:17][NH2:18]>>[Cl:1][C:2]1[S:6][C:5]([S:7](=[O:10])(=[O:9])[NH2:8])=[C:4]([C:11]([NH:17][NH2:18])=[O:13])[CH:3]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10978507HCID 10978507, compound

Product 1

HCID 11807266HCID 11807266, compoundYield 89%

Procedure

Ethyl 5-chloro-2-sulfamoylthiophene-3-carboxylate (50.0 g; 0.185 mol) was added in one portion to 98% hydrazine hydrate (50 ml) with stirring at ambient temperature. The reaction was slightly exothermic. The solution was stirred for 90 min. and concentrated. The residue was crystallised by trituration with 250 ml of water and the mixture was adjusted to pH 2-3 with conc. hydrochloric acid and stirred for 30 min. at 0° C. The product was isolated by filtration, washed with water and dried to give 42.2 g (89%) of the title compound; 1H-NMR (DMSO-d6): δ 4.7 (br. s, 2H, NH2), 7.49 (s, 1H), 7.71 (br. s, 2H, NH2), 9.94 (br. s, 1H, NH).

Workup

  1. stirringThe solution was stirred for 90 min.
  2. concentrationconcentrated
  3. customThe residue was crystallised by trituration with 250 ml of water
  4. stirringstirred for 30 min. at 0° C
  5. customThe product was isolated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-92faea80ba4145dc94e7912fda218b86
Source dataset
uspto-grants-1999_03
Patent number
US05889002

Reaction notes

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