Potassium Carbonate → 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(methylsulfanyl)-1H-benzimidazole

HRID 450140

Reaction equation

HRID 450140 reaction equation
[CH3:1][S:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[N:16]=[C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:12][C:13]1[N:14]=[C:15]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[N:16]=[C:17]([N:7]2[C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[N:4]=[C:3]2[S:2][CH3:1])[N:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 235392-(Methylthio)benzimidazoleHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazine

Product 1

HCID 866497771-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(methylsulfanyl)-1H-benzimidazoleYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(methylsulfanyl)-1H-benzimidazole (1.64 g, 10 mmol), 2,4-dichloro-6-(4-morpholinyl)-1,3,5-triazine (2.35 g, 10 mmol), and powdered K2CO3 (11 g, 80 mmol) in DMF (50 mL) was stirred at room temperature for 1 hr. The mixture was diluted with water and the resulting precipitate was collected, washed with water and then ethanol, and dried to give 3.56 g (98% yield) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(methylsulfanyl)-1H-benzimidazole: mp (CHCl3/EtOH) 260-261° C.; 1H NMR (CDCl3) δ 8.42 (br dd, J=7.0, 1.9 Hz, 1H), 7.65 (br dd, J=6.8, 1.9 Hz, 1H), 7.30 (m, 2H), 4.06 (m, 2H), 3.95 (m, 2H), 3.84 (m, 2H), 3.80 (m, 2H), 2.74 (s, 3H); Anal. Calcd. for C1sH15ClN6OS: C, 49.65; H, 4.2; N, 23.2. Found: C, 49.8; H, 4.1; N, 23.1%.

Workup

  1. customthe resulting precipitate was collected
  2. washwashed with water
  3. dry with materialethanol, and dried

Sources & evidence

ORD record
ord-ccf55f8f1aa442819f121a1e306eb894
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Linked notes

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