Pyrrolidine → HCID 13195107, compound

HRID 435454Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13](Cl)(=[O:15])=[O:14])=[O:11])[N:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:15])=[O:14])=[O:11])[N:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a methylene chloride solution of [(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]sulfamoyl chloride, prepared as in Example 1, was added dropwise 2.9 g of pyrrolidine while maintaining the temperature at 20° C. The mixture was stirred for 16 hours and added to 50 ml of ice-water. Enough methylene chloride was added to dissolve the solids present and the methylene chloride solution was washed twice with equal volumes of water, dried over magnesium sulfate, filtered and evaporated in-vacuo. The residue, m.p. 180°-181° C., showed absorption peaks by infrared spectroscopy at 1690, 1605 and 1550 cm-1 and Nuclear Resonance Spectroscopy (60 MC) at 2.02 δ (mult.) and 3.64 δ (mult.) for the pyrrolidine hydrogens, 2.6 δ (singlet) for CH3 and 6.85 δpyrimidine H with integration ratios of 4:4:6:1, consistent for the desired structure.

Workup

dissolutionto dissolve the solids present
washthe methylene chloride solution was washed twice with equal volumes of water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated in-vacuo
customabsorption peaks by infrared spectroscopy at 1690, 1605 and 1550 cm-1 and Nuclear Resonance Spectroscopy (60 MC) at 2.02 δ (mult.) and 3.64 δ (mult.) for the pyrrolidine hydrogens, 2.6 δ (singlet) for CH3 and 6.85 δpyrimidine H with integration ratios of 4:4:6:1

Sources & evidence

ORD record: ord-96ecf5096ce84fcf8dc8c2d2b53fa65a
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04401816

Reaction notes

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