2-(Dimethylsulfamoyl)benzene-1-sulfonyl isocyanate → N'-[(4-methoxy-6-methylpyrimidin-2-yl)methylaminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide

HRID 1285086Notes

Reaction equation

HRID 1285086 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[N:4]=1.[CH3:12][N:13]([CH3:29])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])(=[O:16])=[O:15]>C(Cl)Cl>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([CH3:9])[N:8]=[C:3]([CH2:2][NH:1][C:27]([NH:26][S:23]([C:18]2[C:17]([S:14]([N:13]([CH3:29])[CH3:12])(=[O:16])=[O:15])=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:25])=[O:24])=[O:28])[N:4]=1

Participants

4

Reactant 2

HCID 133926792-(Dimethylsulfamoyl)benzene-1-sulfonyl isocyanateHCID 13392683(4-Methoxy-6-methylpyrimidin-2-YL)methanamine

Product 1

HCID 13392684N'-[(4-methoxy-6-methylpyrimidin-2-yl)methylaminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamideYield 49.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 9 (0.90 g) was added in a steady stream to a stirred solution of 2.3 g of 2-(N,N-dimethylsulfamoyl)benzenesulfonyl isocyanate in 20 ml dry methylene chloride at room temperature. The reaction solution was stirred for an additional 18 hours and the solvent was removed in vacuo. The resulting yellow foam was stirred with 1-chlorobutane for ca. one hour. The mixture was filtered and the collected solids dried to yield 1.3 g of N'-[(4-methoxy-6-methylpyrimidin-2-yl)methylaminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide, m.p. 153°-156° C., as a light yellow solid.

Workup

  1. customthe solvent was removed in vacuo
  2. stirringThe resulting yellow foam was stirred with 1-chlorobutane for ca. one hour
  3. filtrationThe mixture was filtered
  4. customthe collected solids dried

Sources & evidence

ORD record
ord-f75540589522422f99cd7e52a4e8646a
Source dataset
uspto-grants-1986_01
Patent number
US04565567

Reaction notes

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