Triethylamine → 3-(Pyridine-3-carbonyl)-1,3-thiazolidine-4-carboxylic acid

HRID 1788759Notes

Reaction equation

Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[S:11]1[CH2:15][CH:14]([C:16]([OH:18])=[O:17])[NH:13][CH2:12]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:2]([N:13]1[CH:14]([C:16]([OH:18])=[O:17])[CH2:15][S:11][CH2:12]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

Conditions

Temperature: 64 °C

Procedure

Nicotinoyl chloride hydrochloride (534 g) is added over 1 hour at a temperature of between 30° and 52° C. to a solution of thiazolidine-4-carboxylic acid (400 g) and triethylamine (613 g) in chloroform (4,500 cc). The solution obtained is heated at a temperature of about 64° C. for 4 hours. After stirring at a temperature of about 20° C. for 16 hours, the crystals which have appeared are separated off by filtration, washed 3 times with chloroform (1,500 cc in total), then 3 times with diethyl ether (1,500 cc in total) and are dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. N-nicotinoylthiazolidine-4-carboxylic acid (403 g) is thus obtained in the form of white crystals melting at 190° C.

Workup

customThe solution obtained
customthe crystals which have appeared are separated off by filtration
washwashed 3 times with chloroform (1,500 cc in total)
dry with material3 times with diethyl ether (1,500 cc in total) and are dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record: ord-47cc5b7ec62c400e8d9aa5bf0052b74e
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04684658

Reaction notes

Loading…