2-Amino-4,6-dimethyl pyrimidine → N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(dimethylaminosulfonyloxy)benzenesulfonamide

HRID 482798Notes

Reaction equation

HRID 482798 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][N:11]([CH3:28])[S:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([N:25]=[C:26]=[O:27])(=[O:24])=[O:23])(=[O:14])=[O:13]>C(Cl)Cl>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:26]([NH:25][S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][S:12]([N:11]([CH3:28])[CH3:10])(=[O:13])=[O:14])(=[O:23])=[O:24])=[O:27])[N:3]=1

Participants

4

Reactant 2

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 134731272-(Dimethylaminosulfonyloxy)benzenesulfonyl isocyanate

Product 1

HCID 13473130N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(dimethylaminosulfonyloxy)benzenesulfonamideYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.37 g (0.003 mole) 2-amino-4,6-dimethylpyrimidine in 5 ml methylene chloride was added 1.2 g (0.004 mole) 2-(dimethylaminosulfonyloxy)-benzenesulfonyl isocyanate. The reaction exothermed (18°-26° C.) and was stirred at room temperature for 3 hours. The resultant white precipitate was filtered to give 0.9 g of a white solid, m.p. 195°-196° C. The infrared spectrum shows absorption bands at 1705, 1380, 1180 cm-1. Calc. for: C-41.9; H-4.46; N-16.3; S-14.9. Found: C-41.9; H-4.50; N-15.5; S-14.9.

Workup

  1. filtrationThe resultant white precipitate was filtered

Sources & evidence

ORD record
ord-1a6d30dd417a44e9b6960d0b8ce29fdd
Source dataset
uspto-grants-1986_03
Patent number
US04576633

Reaction notes

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