Methanethiol → N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(methylthio)carbonylbenzenesulfonamide

HRID 66445Notes

Reaction equation

HRID 66445 reaction equation
C[Al](C)C.[Cl:5][C:6]1[C:7]([CH3:30])=[N:8][C:9]([NH:13][C:14]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](OC)=[O:27])(=[O:19])=[O:18])=[O:15])=[N:10][C:11]=1[CH3:12].[CH3:31][SH:32]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:7]([CH3:30])=[N:8][C:9]([NH:13][C:14]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([S:32][CH3:31])=[O:27])(=[O:19])=[O:18])=[O:15])=[N:10][C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 13038397N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 13305297N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(methylthio)carbonylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethylaluminum (6.0 ml, 2 M) is charged via syringe to 15 ml dry toluene under nitrogen atmosphere and 3.8 g N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide is added portionwise. After stirring at room temperature for one hour, methyl mercaptan (gas) is passed through the reaction mixture until the initial temperature rise subsided, whereupon the addition is discontinued. The reaction mixture is allowed to stir at room temperature for 1 hour, and quenched with 25 ml of 10% HCl. The resultant white suspension is filtered to give the desired product.

Workup

  1. additionsubsided, whereupon the addition
  2. stirringto stir at room temperature for 1 hour
  3. customquenched with 25 ml of 10% HCl
  4. filtrationThe resultant white suspension is filtered

Sources & evidence

ORD record
ord-396a985591f743359469f313a441a1cf
Source dataset
uspto-grants-1982_08
Patent number
US04342587

Reaction notes

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