Sodium Hydroxide → HCID 19819855, compound

HRID 1834757Notes

Reaction equation

HRID 1834757 reaction equation
[CH2:1]([S:5]([C:8]1[CH:17]=[CH:16][C:11]([NH:12]C(=O)C)=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[N:18]([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>O.Cl.C(O)C>[CH2:1]([S:5]([C:8]1[CH:17]=[CH:16][C:11]([NH:12][NH2:18])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24437Sodium SulfiteHCID 237535N-[4-(Butane-1-sulfonyl)phenyl]ethanimidic acidHCID 23668193Sodium Nitrite

Product 1

HCID 19819855HCID 19819855, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

255 g of p-butylsulphonylacetanilide, in a mixture of 1.5 l of water and 300 ml of concentrated hydrochloric acid, are boiled for 1 hour under reflux. After cooling to 0° C, the product is diazotised with a solution of 70 g of NaNO2 in 175 ml of water. The filtered diazonium salt solution is added, at 5°-10° C, to a mixture of 750 g of 40% strength sodium sulphite solution and 750 ml of water which had been adjusted to pH 7 with concentrated sodium hydroxide solution, the pH being maintained at 6-7 by means of concentrated sodium hydroxide solution. After standing overnight, 300 ml of concentrated hydrochloric acid are added and the mixture is boiled for 1 hour. p-Butylsulphonylphenylhydrazine of melting point 138° C (from ethanol) is obtained, in a yield of approx. 70- 75% of theory, from the cooled solution by careful addition of alkali.

Workup

  1. temperatureunder reflux
  2. waitAfter standing overnight
  3. waitthe mixture is boiled for 1 hour

Sources & evidence

ORD record
ord-abc88074ae2f4e0bbd6cbe2d758bc98c
Source dataset
uspto-grants-1978_01
Patent number
US04071466

Reaction notes

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