Acetyl chloride → HCID 178432199, compound

HRID 1657383Notes

Reaction equation

HRID 1657383 reaction equation
[S:1]([C:5]1[CH:11]=[C:10]([SH:12])[C:9]([Cl:13])=[CH:8][C:6]=1[NH2:7])(=[O:4])(=[O:3])[NH2:2].[C:14](Cl)(=O)[CH3:15]>O1CCOCC1>[CH3:14][C:15]1[NH:2][S:1](=[O:3])(=[O:4])[C:5]2[CH:11]=[C:10]([SH:12])[C:9]([Cl:13])=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 21533310HCID 21533310, compound

Product 1

HCID 178432199HCID 178432199, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-sulfamoyl-4-mercapto-5-chloroaniline, prepared as described in Example 13, Step A-3 (0.02 mole) and acetyl chloride (0.022 mole) in 75 ml. of dioxane is heated under reflux for 24 hours. The solution is concentrated to dryness in vacuo and the residue dissolved in 75 ml. of ethanol and treated with 75 ml. of concentrated ammonium hydroxide in the cold. Thereafter the solution is heated under reflux for 3 hours and concentrated to dryness in vacuo. The residue is suspended in 100 ml. of water acidified with hydrochloric acid and the product, following recrystallization from dimethylformamide-water, melts at 304°-305° C.

Workup

  1. customprepared
  2. temperatureunder reflux for 24 hours
  3. concentrationThe solution is concentrated to dryness in vacuo
  4. dissolutionthe residue dissolved in 75 ml
  5. additionof ethanol and treated with 75 ml
  6. temperatureThereafter the solution is heated
  7. temperatureunder reflux for 3 hours
  8. concentrationconcentrated to dryness in vacuo
  9. customrecrystallization from dimethylformamide-water, melts at 304°-305° C.

Sources & evidence

ORD record
ord-e6d4b9e1092146d9a0926159d3501ed0
Source dataset
uspto-grants-1976_06
Patent number
US03960854

Reaction notes

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