Dabco → N,N-diethyl-N'[4,5,6-trimethylpyrimidin-2-yl]aminocarbonyl-1,2-benzenedisulfonamide

HRID 2295248Notes

Reaction equation

HRID 2295248 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[C:4]([CH3:10])[N:3]=1.[CH2:11]([N:13]([CH2:29][CH3:30])[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])[CH3:12].C1N2CCN(CC2)C1>C(#N)C>[CH2:29]([N:13]([CH2:11][CH3:12])[S:14]([C:17]1[C:18]([S:23]([NH:26][C:27]([NH:1][C:2]2[N:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[C:4]([CH3:10])[N:3]=2)=[O:28])(=[O:25])=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15])[CH3:30]

Participants

5

Reactant 3

HCID 9237DabcoHCID 122508624,5,6-Trimethylpyrimidin-2-amineHCID 12819607o-N,N-Diethylsulfamoylbenzenesulfonyl isocyanate

Product 1

HCID 13305295N,N-diethyl-N'[4,5,6-trimethylpyrimidin-2-yl]aminocarbonyl-1,2-benzenedisulfonamide

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-a1844df4deaf45dba27848f8cd6443b0
Source dataset
uspto-grants-1984_01
Patent number
US04424073

Reaction notes

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