Methanesulfonyl chloride → HCID 57786380, compound

HRID 1399241Notes

Reaction equation

HRID 1399241 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:17]=3[N:13]2[CH2:12][CH:11]([OH:27])[CH2:10]1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].[C:33](=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:28][S:29]([O:27][CH:11]1[CH2:12][N:13]2[C:14](=[N:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])[C:17]=32)[N:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH2:10][CH2:33]1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 57786209HCID 57786209, compound

Product 1

HCID 57786380HCID 57786380, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-(2,4-dichlorophenyl)-6-(diethylamino)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-3-ol (235 mg, 0.563 mmol) in pyridine (1 mL) was added methanesulfonyl chloride (0.436 mL, 5.63 mmol) at room temperature. The resultant mixture was stirred at room temperature for 30 min. Aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound as an orange amorphous solid (279 mg, 0.560 mmol, 99%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-553c1a2bc3224be7981375ec5fc621de
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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