Hydrochloric Acid → HCID 19905882, compound

HRID 2371654Notes

Reaction equation

[N+:1]([C:4]1[C:9]([NH:10][S:11]([C:14]2[N:18]=[CH:17][NH:16][N:15]=2)(=[O:13])=[O:12])=[C:8]([O:19][CH2:20][C:21]#[CH:22])[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:29][O:30][C:31]1[CH:36]=[C:35]([O:37][CH3:38])[N:34]=[C:33](S(C)(=O)=O)[N:32]=1.Cl>CN(C)C=O>[CH3:29][O:30][C:31]1[CH:36]=[C:35]([O:37][CH3:38])[N:34]=[C:33]([N:16]2[CH:17]=[N:18][C:14]([S:11]([NH:10][C:9]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[O:19][CH2:20][C:21]#[CH:22])(=[O:13])=[O:12])=[N:15]2)[N:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3.23 g (10 mmol) N-(6-nitro-2-propargyloxyphenyl)-1H-1,2,4-triazole-3-sulphonamide and 2.76 g (20 mmol) potassium carbonate in 25 ml dimethylformamide was heated under a protective gas for 10 minutes at 50° C. After cooling to 0° C. and addition of 2.18 g (10 mmol) 4,6-dimethoxy-2-methylsulphonylpyrimidine, the mixture was warmed and stirred for 20 hours. It was then stirred into to 300 ml ice-cold saturated aqueous sodium chloride and acidified with hydrochloric acid (pH 4). The crystals were removed by suction filtration and purified by silica gel chromatography using a mixture of hexane and ethyl acetate (0 to 100% ethyl acetate).

Workup

temperatureAfter cooling to 0° C.
temperaturethe mixture was warmed
customThe crystals were removed by suction filtration
custompurified by silica gel chromatography
additiona mixture of hexane and ethyl acetate (0 to 100% ethyl acetate)

Sources & evidence

ORD record: ord-6428006c9bd1438f8d8a92dd1f6a6197
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05094682

Reaction notes

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