Salicylaldehyde → HCID 136139912, compound

Reaction equation

[CH3:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[CH:8](=O)[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11]>>[CH3:1][C:2]1[S:3][C:4]([CH:7]=[CH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[OH:11])=[N:5][N:6]=1

Participants

Reactant 2

HCID 6998Salicylaldehyde

HCID 969222,5-Dimethyl-1,3,4-thiadiazole

Product 1

HCID 136139912HCID 136139912, compoundYield 56%

Conditions

Temperature: 150 °C

Procedure

570 g (5 moles) of 2,5-dimethyl-1,3,4-thiadiazole and 275 g (2.5 moles) of salicylaldehyde are mixed and slowly heated to 150° C., whilst passing nitrogen through the mixture. After having been kept at 150° C. for 30 hours, the mixture is cooled, excess 2,5-dimethyl-1,3,4-thiadiazole is distilled off and the residue is recrystallized from methylglycol. 304 g of yellow crystals (56% of theory), of melting point 253°-254° C. are obtained.

Workup

temperaturethe mixture is cooled
distillationexcess 2,5-dimethyl-1,3,4-thiadiazole is distilled off
customthe residue is recrystallized from methylglycol

Sources & evidence

ORD record: ord-fc926d233cc94d2e9446caaa25aa7b95
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04353917

Reaction notes

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