(2-Amino-5-bromophenyl)(4-chlorophenyl)methanone → 2-Methyl-propane-2-sulfinic acid (2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyleneamide

HRID 1497713Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=O.[CH3:18][C:19]([S:22]([NH2:24])=[O:23])([CH3:21])[CH3:20]>C1COCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[N:24][S:22]([C:19]([CH3:21])([CH3:20])[CH3:18])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (2-Amino-5-bromo-phenyl)-(4-chloro-phenyl)-methanone (13.87 g, 0.05 mol) in THF (200 mL) is added 2-Methyl-propane-2-sulfinic acid amide (6.5 g, 0.05 mol) and Ti(OEt)4 (20.5 g, 0.09 mol).The stirred mixture is refluxed at 80° C. The mixture is quenched with H2O, filtered. THF is removed, extracted with ethyl acetate, dried over NaSO4 and concentrated then purified by silica gel. This produces the desired compound.

Workup

customThe mixture is quenched with H2O
filtrationfiltered
customTHF is removed
extractionextracted with ethyl acetate
dry with materialdried over NaSO4
concentrationconcentrated
customthen purified by silica gel

Sources & evidence

ORD record: ord-b1e1fe71f526430e872375e4ddd15dbb
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199988B2

Reaction notes

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