Water → HCID 54175266, compound

HRID 1449235Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[C:12]([S:15]([CH3:17])=[O:16])[S:13][CH3:14].[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C>[CH2:25]([N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[C:12]([S:15]([CH3:17])=[O:16])[S:13][CH3:14])[C:3]1[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:2]=1[Cl:1])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In 25 ml of DMF, 3.8 g (0.010 mole) of 1-[o-(2,6-dichloroanilino)phenyl]-2-methylsulfinyl-2-methylthioethylene was dissolved and 0.98 g (0.022 mole) of sodium hydride (55%; oil dispersion) was added at 20° to 30° C. and the mixture was stirred at 80° C. for 1 hour and cooled to 20° C. and 44 g (0.026 mole) of benzyl bromide was further added and the mixture was stirred at room temperature (20° to 30° C.) for 12 hours and the reaction mixture was poured into a large amount of water to precipitate yellow crystals and the resulting crystals were filtered and dried under a reduced pressure and further recrystallized from benzene to obtain 4.5 g of 1-[N-benzyl-o-(2,6-dichloroanilino)phenyl]-2-methylsulfinyl-2-methylthioethylene as pale yellow crystals. Yield: 98%

Workup

temperaturecooled to 20° C.
stirringthe mixture was stirred at room temperature (20° to 30° C.) for 12 hours
customto precipitate yellow crystals
filtrationthe resulting crystals were filtered
customdried under a reduced pressure
customfurther recrystallized from benzene

Sources & evidence

ORD record: ord-b05ecbc04d2f44999461baae0e019d6f
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04189595

Reaction notes

Loading…