Sodium Bicarbonate → 4-(4-Chloro-3-sulfamoylphenyl)-2-isopropylimino-3-methyl-1,3-thiazolidine-4-ol

HRID 1703846

Reaction equation

Br.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:19])[CH2:13][S:12][C:11](=[N:14][CH:15]([CH3:17])[CH3:16])[N:10]2[CH3:18])=[CH:5][C:4]=1[S:20](=[O:23])(=[O:22])[NH2:21].C(=O)(O)[O-].[Na+]>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:19])[CH2:13][S:12][C:11](=[N:14][CH:15]([CH3:17])[CH3:16])[N:10]2[CH3:18])=[CH:5][C:4]=1[S:20](=[O:22])(=[O:23])[NH2:21]

Participants

Conditions

Temperature: 40 °C

Procedure

7 g of ground 4-(4-chloro-3-sulfamoylphenyl)-2-isopropylimino-3-methyl-1,3-thiazolidine-4-ol-hydrobromide were dissolved in 80 ml of 40° C. hot water and stirred for 30 minutes at 40° C. after adding it to a mixture of 60 ml of saturated sodium bicarbonate solution and 100 ml of water. After cooling to room temperature, the mixture was extracted with 200 ml of diethyl ether, the organic phase was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The residue was dissolved in 40 ml of diisopropyl ether and the end product was precipitated by pouring it into 200 ml of stirred petroleum ether. Colorless solid body: decomposition beginning at 100° C., γC=N 1610 cm-1.

Workup

additionafter adding it
temperatureAfter cooling to room temperature
extractionthe mixture was extracted with 200 ml of diethyl ether
dry with materialthe organic phase was dried over sodium sulfate
distillationthe solvent was distilled off under reduced pressure
dissolutionThe residue was dissolved in 40 ml of diisopropyl ether
customthe end product was precipitated
additionby pouring it into 200 ml of stirred petroleum ether
custombeginning at 100° C.

Sources & evidence

ORD record: ord-b09903bc1023469f93d399d0b1e39950
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04125614

Linked notes

Loading…