Triethylamine → N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-chloro-benzenesulfonamide

HRID 378287Notes

Reaction equation

HRID 378287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH:19][CH3:20])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.CN.[CH2:24]([N:26](CC)CC)C>C(O)C>[CH3:20][NH:19][C:14]1[N:13]=[C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:17]=[C:16]([NH:26][CH3:24])[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 193535554-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

Product 1

HCID 17774528N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-chloro-benzenesulfonamideYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

0.62 g (0.0019 mol) of 4-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide was dissolved in 10 ml of ethanol, treated with 1.67 g (0.025 mol) of methylamine hydrochloride and 6.2 ml (0.044 mol) of triethylamine and stirred in an autoclave at 140° C. for 18 hours. The mixture was freed completely from solvent, the residue was partitioned in ethyl acetate/water and the insoluble constituents were filtered off under suction. The filter cake was recrystallized in methanol/diethyl ether. There was obtained 0.28 g (45%) of N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-chloro-benzenesulfonamide as white crystals; m.p. 272-273° C.

Workup

  1. customthe residue was partitioned in ethyl acetate/water
  2. filtrationthe insoluble constituents were filtered off under suction
  3. customThe filter cake was recrystallized in methanol/diethyl ether

Sources & evidence

ORD record
ord-b19d8bc201604946b3d9f6e15227402e
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

Loading…