Water → HCID 178514681, compound

HRID 904851Notes

Reaction equation

HRID 904851 reaction equation
[OH-].[K+].O.[C:4](=S)=[S:5].[NH2:7][C:8]1[CH:14]=[C:13]([Cl:15])[C:12]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:11][C:9]=1[NH2:10]>C(O)C.CO>[Cl:15][C:13]1[C:12]([S:16](=[O:18])(=[O:19])[NH2:17])=[CH:11][C:9]2[NH:10][C:4]([SH:5])=[N:7][C:8]=2[CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamide

Product 1

HCID 178514681HCID 178514681, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

To 2.9 g of potassium hydroxide dissolved in 45 ml of ethanol and 9 ml of water was added with stirring 4.0 g of carbon disulfide. This solution was then added dropwise to 300 ml of ethanol containing 11.8 g of 2-amino-4-chloro-5-sulfamylaniline. The reaction was refluxed for 5 hours and then concentrated in vacuo to a dark oil. Treatment with 50° C. water provided a solid which was removed by filtration. The filtrate was cooled with ice and acidified to pH 5.0 with acetic acid to yield a gray solid. Trituration of the solid with boiling methanol provided a solid which upon drying gave 5.6 g of pink crystals, m.p. 341°-343°.

Workup

  1. temperatureThe reaction was refluxed for 5 hours
  2. concentrationconcentrated in vacuo to a dark oil
  3. customTreatment with 50° C. water provided a solid which
  4. customwas removed by filtration
  5. temperatureThe filtrate was cooled with ice
  6. customto yield a gray solid
  7. customupon drying

Sources & evidence

ORD record
ord-9ce6a0d629074252bb2c85fbd74c6660
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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