Benzothiazole → N-Allylbenzothiazolium Bromide

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH2:10]([Br:13])[CH:11]=[CH2:12]>>[Br-:13].[CH2:12]([N+:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH:2]=1)[CH:11]=[CH2:10]

Participants

Reactant 2

HCID 7222Benzothiazole

HCID 7841Allyl bromide

Product 1

HCID 177743N-Allylbenzothiazolium Bromide

Procedure

135 g of benzothiazole and 121 g of allylbromide were mixed and the mixture was heated for 2 hours on a steam bath to solidify by crystallization. After cooling, diethyl ether was added to wash the crystals. After filtration and drying, the crystals obtained were recrystallized from ethanol. Melting point: 145°-147°C.

Workup

temperaturethe mixture was heated for 2 hours on a steam bath
customto solidify by crystallization
temperatureAfter cooling
additiondiethyl ether was added
washto wash the crystals
filtrationAfter filtration
customdrying
customthe crystals obtained
customwere recrystallized from ethanol

Sources & evidence

ORD record: ord-bacc7980f0ac48e1bad84dc4e8621280
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03954478

Reaction notes

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