Sulfuric Acid → N-(3'-bromo-1',1'-dimethylacetonyl)-3,5-dichlorobenzamide

HRID 1780004Notes

Reaction equation

Br.[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[O:11][C:12](=[CH:17][Br:18])[C:13]([CH3:16])([CH3:15])[N:14]=2)[CH:6]=[C:7]([Cl:9])[CH:8]=1.S(=O)(=O)(O)[OH:20]>O>[Br:18][CH2:17][C:12](=[O:11])[C:13]([NH:14][C:10](=[O:20])[C:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[C:7]([Cl:9])[CH:6]=1)([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

N- (1',1'-dimethylpropynyl)-3,5-dichlorobenzamide (40 gm, 0.156 m) was dissolved in methylene chloride (600 ml) and bromine (25 gm, 0.156 m) in methylene chloride (100 ml) was added gradually with stirring at room temperature. After the complete addition of the bromine, the mixture was stirred for another 15 minutes and diluted with hexane (500 ml). The yellowish-white precipitate which formed was filtered and dried to yield 58 gm of 2-(3',5'-dichlorophenyl)-4,4-dimethyl-5-bromomethylenoxazoline hydrobromide. The oxazoline hydrobromide (55 gm, 0.13 m) was added to concentrated sulfuric acid (200 ml) and stirred to obtain a clear solution. Water (20 ml) was added and the mixture heated at about 50° C. for about 24 hours. The mixture was then poured into ice water (about 2000 ml) and the white precipitate which formed was filtered and dried. Recrystallization from isopropanol, ether and hexane (1:1:2) yielded 21 gm of pure product.

Workup

customto obtain a clear solution
customthe white precipitate which formed
filtrationwas filtered
customdried
customRecrystallization from isopropanol, ether and hexane (1:1:2)

Sources & evidence

ORD record: ord-cb2d9d6669174a4a9f9f3acd07807f6b
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629346

Reaction notes

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