Carbon Disulfide → potassium N-(2-biphenylylsulfonyl)carbonimidodithioate

HRID 1589087Notes

Reaction equation

HRID 1589087 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([NH2:16])(=[O:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](=[S:19])=[S:18].[OH-].[K+:21].C(OCC)(=O)C>CN(C)C=O>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([N:16]=[C:17]([S-:19])[S-:18])(=[O:14])=[O:15].[K+:21].[K+:21]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8857Ethyl AcetateHCID 14797Potassium Hydroxide2×HCID 123715202-Phenylbenzene-1-sulfonamide

Product 1

HCID 13422022potassium N-(2-biphenylylsulfonyl)carbonimidodithioateYield 166.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

115.5 g of 2-phenylbenzenesulfonamide were dissolved in 500 ml of dimethylformamide, and 38 g of carbon disulfide and 28 g of potassium hydroxide were added to the resulting solution. The mixture was stirred at room temperature for 7 hours. Potassium hydroxide (28 g) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. Then, 400 ml of ethyl acetate were added dropwise to precipitate pale yellow crystals. The crystals were filtered, and washed with ethyl acetate to give 160 g of potassium N-(2-biphenylylsulfonyl)carbonimidodithioate represented by the following formula: ##STR25##

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customto precipitate pale yellow crystals
  3. filtrationThe crystals were filtered
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7e3ce940ecbe4ae2961445c0e00f98f5
Source dataset
uspto-grants-1986_02
Patent number
US04568381

Reaction notes

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