Hydrochloric Acid → HCID 178503936, compound

HRID 1906296Notes

Reaction equation

HRID 1906296 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH3:13][S:14][C:15](SC)=[N:16][C:17]#[N:18].[OH-].[Na+].Cl>C(O)C.O>[C:17]([N:16]=[C:15]([S:14][CH3:13])[NH:12][S:9]([C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:10])=[O:11])#[N:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 2380452,5-Dichlorobenzenesulfonamide

Product 1

HCID 178503936HCID 178503936, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 10.6 g (43.2 mmol) of 2,5-dichlorobenzenesulfonamide, 7.15 g (44.0 mmol) of 90 percent dimethyl N-cyanodithioiminocarbonate and 1.8 g (44 mmol) of NaOH in 60 ml of ethanol and 10 ml of H2O was heated at reflux for 6 hours. After cooling to room temperature the reaction mixture was poured into 600 ml of ice water. The resulting solution was acidified with 6N HCl to separate 2.2 g of the desired product as a white solid. Concentration of the filtrate gave an additional 8.5 g of the desired product. The total yield of material was 10.7 g (76 percent) of white solid, mp 145° C. IR and 1H NMR spectra were consistent with the assigned structure.

Workup

  1. temperatureat reflux for 6 hours
  2. customto separate 2.2 g of the desired product as a white solid

Sources & evidence

ORD record
ord-14a24c0f8cf140e895ae49d102e0ceea
Source dataset
uspto-grants-1987_03
Patent number
US04650892

Reaction notes

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