Hydrochloric Acid → 3-Carboxymethyl-5-(2,2-dimethylpropylidene)rhodanine

HRID 64685

Reaction equation

[C:1]([CH2:4][N:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]1=[S:11])([OH:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH3:18][C:19]([CH3:23])([CH3:22])[CH:20]=O.Cl>O.CN(C=O)C>[C:1]([CH2:4][N:5]1[C:9](=[O:10])[C:8](=[CH:18][C:19]([CH3:23])([CH3:22])[CH3:20])[S:7][C:6]1=[S:11])([OH:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

Into 20 ml of dry DMF was dissolved 1.5 g (0.008 mole) of 3-carboxymethylrhodanine. To the solution was added 2.2 g (0.016 mole) of K2CO3 at a room temperature, and further 1 g (0.012 mole) of 2,2-dimethylpropanal was added dropwise at 60° C. After agitating at 60° C. for 30 minutes, the reaction mixture was poured into water. The resultant was adjusted to pH 4 with a dilute hydrochloric acid and then extracted with ethyl acetate. The extract was purified through a silica gel column and recrystallized from a mixed solvent of ethyl acetate and ethanol to give 1.3 g of 3-carboxymethyl-5-(2,2-dimethylpropylidene)rhodanine in the form of light yellow needle (yield: 63%).

Workup

extractionextracted with ethyl acetate
customThe extract was purified through a silica gel column
customrecrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record: ord-7c6c6c5c2879429d939127f5a9ef0417
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04609736

Linked notes

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