Diethyl Ether → HCID 178479417, compound

HRID 1196619Notes

Reaction equation

Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC(C)([O-])C.[K+].[Cl:12]C1C(C)=CC=C(Cl)C=1NC1C=CC=CC=1[C:28]1[N:32]=[C:31](S(C2C=CC(C)=CC=2)(=O)=O)[S:30][N:29]=1.CCOCC>C(O)(C)(C)C>[ClH:12].[S:30]1[C:31]([NH:4][C:3]([NH2:5])=[NH:2])=[N:32][CH:28]=[N:29]1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of guanidine hydrochloride (197 mg, 2.06 mmols) and potassium t-butoxide (150 mg, 1.33 mmols) in 10 mL of t-butanol is heated to 40° C. 2,6-Dichloro-3-methyl-N-[2-[5-[(4-methylphenyl)-sulfonyl]-1,2,4-thiadiazol-3-yl]phenyl]benzenamine (200 mg, 0.41 mmols), prepared as described in Example 2, is added and heating is continued at 55° C. for 10 minutes. The solution is cooled to room temperature, poured into ether, and washed with water followed by brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated to 10 mL. A few drops of methanol saturated with HCl are added. The resultant precipitate is collected by filtration, providing 84 mg (48%) of 3-[2-[2,6-dichloro-3-methylphenyl)amino]phenyl]-1,2,4-thiadiazol-5-yl guanidine, monohydrochloride as a white solid; mp 268°-277° C.

Workup

additionis added
temperatureheating
temperatureThe solution is cooled to room temperature
washwashed with water
dry with materialThe organic layer is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated to 10 mL
additionA few drops of methanol saturated with HCl are added
filtrationThe resultant precipitate is collected by filtration

Sources & evidence

ORD record: ord-7164da15f3e9422596d5de0b9927df40
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05114958

Reaction notes

Loading…