Dimethylamine → (Dihydro-3,3-diphenyl-3H-furan-2-ylidene)dimethylammonium bromide

HRID 279074

Reaction equation

[CH3:1][NH:2][CH3:3].C(=O)([O-])[O-].[Na+].[Na+].[Br:10][CH2:11][CH2:12][C:13]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](Cl)=[O:15]>O.C1(C)C=CC=CC=1>[Br-:10].[CH3:1][N+:2]([CH3:3])=[C:14]1[C:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11][O:15]1

Participants

Conditions

Temperature: 2.5 °C

Procedure

In 100 mL of water were suspended 8 g (90 mmol) of a 50% aqueous solution of dimethylamine and 18 g (170 mmol) of sodium carbonate, followed by cooling to 0 to 5° C. A solution obtained by dissolving 23 g (68 mmol) of the 4-bromo-2,2-diphenylbutyric chloride mentioned above in 100 mL of toluene was then added dropwise. After stirring for 2 hours, the water layer taken out from the reaction mixture was washed with toluene. The resulting water layer was extracted with chloroform. The extract was washed with water and then dried. The residue obtained by concentrating the solvent under reduced pressure was crystallized from methyl isobutyl ketone, whereby 11 g (yield: 46.8%) of dimethyl(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide was obtained.

Workup

customA solution obtained
additionwas then added dropwise
washwas washed with toluene
extractionThe resulting water layer was extracted with chloroform
washThe extract was washed with water
customdried
customThe residue obtained
concentrationby concentrating the solvent under reduced pressure
customwas crystallized from methyl isobutyl ketone

Sources & evidence

ORD record: ord-59e7d6bdf1514172bcd3af8ded68a246
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362203B1

Linked notes

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