Malonic Acid → beta-(2-Methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazol-5-yl)-propenoic acid

HRID 326086Notes

Reaction equation

[CH3:1][C:2]1[S:6][C:5]2=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([CH:10]=O)[N:4]2[N:3]=1.C(O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1>N1C=CC=CC=1>[CH3:1][C:2]1[S:6][C:5]2=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([CH:10]=[CH:19][C:20]([OH:22])=[O:21])[N:4]2[N:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

90 g of 2-methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazole-5-carbaldehyde, 60 g of malonic acid and 3 ml of piperidine in 95 ml of pyridine were boiled under reflux for 10 hours. The mixture was cooled to 5° C., stirred at this temperature for 2 hours and filtered. The residue was washed with water and dried. 92 g (84% of theory) of β-(2-methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazol-5-yl)-propenoic acid of melting point 278°-280° C. (decomposition) were obtained.

Workup

temperatureunder reflux for 10 hours
filtrationfiltered
washThe residue was washed with water
customdried

Sources & evidence

ORD record: ord-6401e28dd4564e7b92e514078c080550
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04444770

Reaction notes

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