Potassium Carbonate → Fexinidazole Sulfone

HRID 437581Notes

Reaction equation

HRID 437581 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10]Cl.[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10][O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([CH3:12])(=[O:15])=[O:14])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1233504-(Methylsulfonyl)phenolHCID 130321332-(Chloromethyl)-1-methyl-5-nitro-1H-imidazole

Product 1

HCID 21429076Fexinidazole Sulfone

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

17.6 Grams (0.1 mole) of 1-methyl-2-chloromethyl-5-nitro-imidazole were heated for 2 hours at a temperature of from 50° to 60° C, while stirring thoroughly, as has been described in detail in Example 2 above, together with 17.2 g (0.1 mole) of 4-methylsulfonylphenol in 50 ml of dimethylacetamide, in the presence of 13.8 g (0.1 mole) of potassium carbonate. According to the processing method described in Example 1 above, 22.5 g (= 73% of the theory) of 1-methyl-2-(4-methylsulfonyl-phenoxymethyl)-5-nitro-imidazole were obtained in the form of white crystals having a melting point of 157° C.

Sources & evidence

ORD record
ord-2c608939de2c4e9c908c3e4467b73396
Source dataset
uspto-grants-1977_06
Patent number
US04031232

Reaction notes

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