2-Nitrobenzenesulfonyl isocyanate → HCID 20189869, compound

HRID 1788625Notes

Reaction equation

HRID 1788625 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([S:9][CH2:10][CH2:11][O:12][CH3:13])[CH:6]=[C:5]([CH3:14])[N:4]=1.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([N:27]=[C:28]=[O:29])(=[O:26])=[O:25])([O-:17])=[O:16]>C(Cl)Cl>[CH3:13][O:12][CH2:11][CH2:10][S:9][C:7]1[CH:6]=[C:5]([CH3:14])[N:4]=[C:3]([N:2]([CH3:1])[C:28]([NH:27][S:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N+:15]([O-:17])=[O:16])(=[O:26])=[O:25])=[O:29])[N:8]=1

Participants

4

Reactant 2

HCID 111388842-Nitrobenzenesulfonyl isocyanateHCID 20189878HCID 20189878, compound

Product 1

HCID 20189869HCID 20189869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By using the procedure of Equation 2 with an equivalent amount of appropriate 2-methylaminopyrimidines or 2-methylamino-1,3,5-triazines and appropriately substituted benzenesulfonylisocyanates or isothiocyanates, the compounds of Table 3 can be prepared. For example, to a dry stirred solution of 19.7 parts of 2-methylamino-4-(2-methoxyethylthio)-6-methylpyrimidine in 300 parts of methylene chloride at ambient temperature is added 22.8 parts of 2-nitrobenzenesulfonylisocyanate. That mixture is stirred and refluxed for 4 hours, and then the methylene chloride is removed under reduced pressure. The resulting solid is triturated with 1-chlorobutane to yield N-[N-[4-(2-methoxyethylthio)-6-methylpyrimidin-2-yl]-N-methylaminocarbonyl]-2-nitrobenzenesulfonamide.

Workup

  1. customthe compounds of Table 3 can be prepared
  2. customat ambient temperature
  3. temperaturerefluxed for 4 hours
  4. customthe methylene chloride is removed under reduced pressure
  5. customThe resulting solid is triturated with 1-chlorobutane

Sources & evidence

ORD record
ord-6e67689ddc2b42cbafc28f9da9834950
Source dataset
uspto-grants-1987_08
Patent number
US04684395

Reaction notes

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