Benzyl Bromide → HCID 54175266, compound

HRID 1449234Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[NH:11][C:12]1[C:13](=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:14]=O.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:28][S:29][CH2:30][S:31](=[O:33])[CH3:32]>CN(C)C=O>[CH2:20]([N:11]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[C:30]([S:31]([CH3:32])=[O:33])[S:29][CH3:28])[C:5]1[C:4]([Cl:3])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

In 133 g of dimethylformamide (DMF), 22 g of sodium hydride (55%; oil dispersion) was dispersed and the dispersion was cooled to lower than 25° C., and a solution of 133 g of N-(2,6-dichlorophenyl)anthranilaldehyde in 266 g of DMF was added dropwise during 30 minutes to the dispersion and then 85.5 g of benzyl bromide was added dropwise during 30 minutes and the mixture was stirred at 20° C. for 1 hour and 22 g of sodium hydride (55%; oil dispersion) was added and then, 62 g of formaldehyde dimethyl mercaptal S-oxide was added dropwise during 1 hour at the reaction temperature of lower than 25° C. The precipitate was filtered and washed with methanol and water and dried under a reduced pressure to obtain 210.2 g of 1-[N-benzyl-o-(2,6-dichloroanilino)phenyl]2-methylsulfinyl-2-methylthioethylene as pale yellow crystals. Melting point 194° to 196° C. (benzene)

Workup

filtrationThe precipitate was filtered
washwashed with methanol and water
customdried under a reduced pressure

Sources & evidence

ORD record: ord-bd050b22b49f45f5a24abcaa517a857d
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04189595

Reaction notes

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