Phenylsulphonyl isocyanate → N-[(4-Dimethylamino-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 1449315Notes

Reaction equation

HRID 1449315 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([CH3:11])[N:3]=1.[C:12]1([S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl.CC(C)=O>[CH3:9][N:8]([CH3:10])[C:6]1[CH:5]=[C:4]([CH3:11])[N:3]=[C:2]([NH:1][C:22]([NH:21][S:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:20])=[O:19])=[O:23])[N:7]=1

Participants

5

Reactant 2

HCID 76096Phenylsulphonyl isocyanateHCID 137293006,N4,N4-trimethyl-pyrimidine-2,4-diamine

Product 1

HCID 23332186N-[(4-Dimethylamino-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 15.2 g of 2-amino-4-dimethylamino-6-methylpyrimidine in 400 ml of methylene chloride at ambient temperature was added slowly 18.3 g of benzenesulfonylisocyanate. After stirring for four hours the mixture was stripped in-vacuo and the white semisolid residue triturated with ethyl ether and isolated by filtration. The solid was then slurried in hot acetone, cooled and refiltered to yield the solid named above which decomposed at 180°-182°.

Workup

  1. customthe white semisolid residue triturated with ethyl ether
  2. customisolated by filtration
  3. temperaturecooled
  4. customto yield the solid
  5. customdecomposed at 180°-182°

Sources & evidence

ORD record
ord-87b3baa3551f4220bf81b7b8ae9dccc7
Source dataset
uspto-grants-1980_02
Patent number
US04190432

Reaction notes

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