Triethylamine → 3-Ethyl-2-ethylimino-4-(4-chloro-3-sulfamoylphenyl)-1,3-thiazolidine-4-ol-hydrochloride

HRID 1703842Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

17 g of 3-ethyl-2-ethylimino-4-(4-chloro-3-sulfamoylphenyl)-1,3-thiazolidine-4-ol-hydrobromide were suspensed in 100 ml of methanol and shortly heated to boiling after the addition of 10 ml of triethyl amine. The solvent was distilled off under reduced pressure, 150 ml of water were added to the residue and the mixture was extracted with 200 ml of ethyl acetate. After drying the organic phase over sodium sulfate the solvent was distilled off under reduced pressure. The residue was dissolved in 100 ml of acetone, the solution was acidified with 15% ethanolic HCl and the oily precipitate of the end product was crystallized with acetone heated to 40° C. Melting point: 177° C. (decomposition).

Workup

temperatureshortly heated
distillationThe solvent was distilled off under reduced pressure, 150 ml of water
additionwere added to the residue
extractionthe mixture was extracted with 200 ml of ethyl acetate
dry with materialAfter drying the organic phase over sodium sulfate the solvent
distillationwas distilled off under reduced pressure
dissolutionThe residue was dissolved in 100 ml of acetone
customthe oily precipitate of the end product was crystallized with acetone

Sources & evidence

ORD record: ord-5eb6cd53d8b84e60833fef1ab9224fd7
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04125614

Reaction notes

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