Methyl 4-carbamothioylbenzoate → Methyl 4-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]benzoate

HRID 1354463Notes

Reaction equation

C(=N[N:9]=[C:10](Cl)[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)C1C=CC=CC=1.[C:22]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)(=[S:24])[NH2:23]>CO>[F:18][C:17]([F:19])([F:20])[C:14]1[CH:13]=[CH:12][C:11]([C:10]2[S:24][C:22]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=3)=[N:23][N:9]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-benzylidene-4-trifluoromethylbenzenecarbohydrazonoyl chloride (1.55 g), methyl 4-thiocarbamoylbenzoate (0.976 g) and methanol (50 ml) was stirred at 50° C. for 2 hrs. After cooling, the crystals were collected by filtration to give methyl 4-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]benzoate (1.03 g, yield 57%) as a colorless crystalline powder. melting point: 218–219° C.

Workup

temperatureAfter cooling
filtrationthe crystals were collected by filtration

Sources & evidence

ORD record: ord-c6b70ee12ee84b749f89a8177368b91a
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223791B2

Reaction notes

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