Hydrazine hydrate (1:1) → HCID 20439474, compound

HRID 1979604Notes

Reaction equation

HRID 1979604 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12].O.[NH2:16][NH2:17]>C(O)C>[NH:16]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12])[NH2:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 667842-Chloro-5-nitrobenzenesulfonamide

Product 1

HCID 20439474HCID 20439474, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-5-nitrobenzenesulphonamide (3.35 g, 14.2 mmole) was dissolved in ethanol (75 ml) with heating and hydrazine hydrate (5 ml. 100 mmole) added. The mixture was refluxed for 45 minutes and then allowed to cool to room temperature. The product cystallised in long needles, 2.4 g. A second crop was obtained on cooling the filtrate in an ice bath, 0.5 g. The combined crops were recrystallised from water (120 ml) to afford pure 2-hydrazino-5-nitrobenzenesulphonamide, m.p. 209°-210° C., 1.85 gm, 60% as orange-yellow needles. TLC analysis (EtOAc:petrol, 1:1) showed one spot (Rf =0.3). Spectroscopic data was consistent with the product.

Workup

  1. temperaturewith heating
  2. temperatureThe mixture was refluxed for 45 minutes
  3. customA second crop was obtained
  4. temperatureon cooling the filtrate in an ice bath
  5. customThe combined crops were recrystallised from water (120 ml)

Sources & evidence

ORD record
ord-bdbf662703b44efbac2f57fa1f605a28
Source dataset
uspto-grants-1984_11
Patent number
US04481268

Reaction notes

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