Triethylamine → N-(2,6-bis-methylamino-pyrimidin-4-yl)-3-chloro-benzenesulfonamide

HRID 610823Notes

Reaction equation

HRID 610823 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.Cl.CN.[CH2:24]([N:26](CC)CC)C>CCO>[CH3:20][NH:19][C:14]1[N:13]=[C:12]([NH:11][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)(=[O:10])=[O:9])[CH:17]=[C:16]([NH:26][CH3:24])[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 193535593-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

Product 1

HCID 17774520N-(2,6-bis-methylamino-pyrimidin-4-yl)-3-chloro-benzenesulfonamideYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

0.10 g (0.00030 mol) of 3-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide was dissolved in 5 ml of EtOH, treated with 0.27 g (0.004 mol) of methylamine hydrochloride and 1 ml (0.007 mol) of triethylamine and stirred in an autoclave at 145° C. for 17 hours. The entire reaction mixture was partitioned in ethyl acetate/water and extracted. The residue was recrystallized from MeOH. There was obtained 0.04 g (41%) of N-(2,6-bis-methylamino-pyrimidin-4-yl)-3-chloro-benzenesulfonamide as white crystals; m.p. 167-168° C.

Workup

  1. customThe entire reaction mixture
  2. customwas partitioned in ethyl acetate/water
  3. extractionextracted
  4. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-8b3a502dc863485aa077787d516b559e
Source dataset
uspto-grants-1999_12
Patent number
US05998665

Reaction notes

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