Dabco → 2-[(dimethylamino)sulfonylmethyl]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 434462Notes

Reaction equation

HRID 434462 reaction equation
[CH3:1][N:2]([CH3:19])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14])(=[O:5])=[O:4].[NH2:20][C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1.C1N2CCN(CC2)C1>C(#N)C>[CH3:1][N:2]([CH3:19])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH:16][C:17]([NH:20][C:21]1[N:22]=[C:23]([O:29][CH3:30])[CH:24]=[C:25]([O:27][CH3:28])[N:26]=1)=[O:18])(=[O:14])=[O:15])(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 9237DabcoHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 131787292-[(Dimethylsulfamoyl)methyl]benzene-1-sulfonyl isocyanate

Product 1

HCID 204925842-[(dimethylamino)sulfonylmethyl]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamideYield 78.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.6 g of the product of Example 5, 0.9 g of 2-amino-4,6-dimethoxypyrimidine and a few crystals of DABCO in 15 ml of dry acetonitrile was heated at 50°-55° for 1 hour under a nitrogen atmosphere, then stirred overnight at room temperature. The precipitate was filtered off, washed with acetonitrile and dried to give 2.1 g of 2-[(dimethylamino)sulfonylmethyl]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, m.p. 172°-176°.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with acetonitrile
  3. customdried

Sources & evidence

ORD record
ord-8dec5d50d7f140b5a4959d613fded792
Source dataset
uspto-grants-1983_08
Patent number
US04397679

Reaction notes

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