Dabco → Benzene-1,2-disulfonamide

HRID 66447

Reaction equation

HRID 66447 reaction equation
NC1N=[C:6]([CH3:8])[C:5](C)=[C:4](C)N=1.[S:11]([N:17]=C=O)(N=C=O)(=[O:13])=[O:12].C1N2[CH2:26][CH2:27]N(CC2)C1>C(#N)C>[C:4]1([S:11]([NH2:17])(=[O:13])=[O:12])[C:5]([S:11]([NH2:17])(=[O:13])=[O:12])=[CH:6][CH:8]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 77898Sulphonyl diisocyanateHCID 122508624,5,6-Trimethylpyrimidin-2-amine

Product 1

HCID 13885364Benzene-1,2-disulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.8 g of 2-amino-4,5,6-trimethylpyrimidine, 2.8 g of the crude sulfonyl isocyanate from Example 9 and a few crystals of DABCO in 25 ml of acetonitrile is stirred at room temperature for 16 hours. A small amount of unreacted aminopyrimidine is filtered off and the filtrate concentrated in-vacuo to give a hard glass. Crystallization from methanol gives N,N-diethyl-N'[4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide as a white solid.

Workup

  1. filtrationA small amount of unreacted aminopyrimidine is filtered off
  2. concentrationthe filtrate concentrated in-vacuo
  3. customto give a hard glass
  4. customCrystallization from methanol

Sources & evidence

ORD record
ord-1444c1eac8794057a4dcdddb36f4a749
Source dataset
uspto-grants-1982_08
Patent number
US04342587

Linked notes

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