Methanesulfonic Acid → 5-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]-1,3,4-thiadiazol-2-amine
Reaction equation
CS(O)(=O)=O.[NH2:6][C:7](=[S:28])[NH:8][NH:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[C:20]([CH3:25])[C:19]=1[Cl:26]>C1(C)C=CC=CC=1>[Cl:26][C:19]1[C:20]([CH3:25])=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[S:28][C:7]([NH2:6])=[N:8][N:9]=1Participants
Procedure
Methanesulfonic acid (280 μl, 4.31 mol) is added dropwise to a suspension of 2-[(2,6-dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide (1.008 g, 2.73 mmol) in 30 ml of toluene. The mixture is heated at reflux for three hours under a nitrogen atmosphere and allowed to cool to room temperature overnight. The tan solid is filtered off and suspended in 100 ml of ethyl acetate. The suspension is then stirred vigorously with 40 ml of 10% aqueous ammonium hydroxide, and the layers are separated. The ethyl acetate layer is washed with water, and dried over magnesium sulfate. Filtration and concentration in vacuo gives a white solid. Drying at 60° C. in vacuo overnight provides 560.8 mg (59%) of product, mp 219°-226° C.
Workup
- temperatureThe mixture is heated
- temperatureat reflux for three hours under a nitrogen atmosphere
- filtrationThe tan solid is filtered off
- customthe layers are separated
- washThe ethyl acetate layer is washed with water
- dry with materialdried over magnesium sulfate
- filtrationFiltration and concentration in vacuo
- customgives a white solid
- customDrying at 60° C. in vacuo overnight
Sources & evidence
- ORD record
- ord-370bc1a58f0947b6a5efff668ee8450b
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05462952
Reaction notes
Loading…