2-Methylbenzothiazole → Benzothiazolium, 3-(2-hydroxyethyl)-2-methyl-, bromide (1:1)
Reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:11][CH2:12][CH2:13][OH:14]>C(OCC)(=O)C>[Br-:11].[OH:14][CH2:13][CH2:12][N+:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A solution of 2-methylbenzothiazole (5.87 g) and 2-bromoethanol (49.2 g) was stirred and heated in an oil bath at 110° C. for 18 hours. After cooling the reaction mixture to room temperature, adding ethyl acetate (100 ml), and decanting, the resultant solid was then dissolved in methanol (50 ml) and precipitated with ethyl acetate (300 ml). The solid was again recrystallized from a mixture of methanol and ethyl acetate, washed with ethyl acetate (2×25 ml) and dried in an oven under high vacuum at 50° C. overnight to obtain 4.21 g (39%) of 4a.
Workup
- temperatureAfter cooling the reaction mixture to room temperature
- customdecanting
- dissolutionthe resultant solid was then dissolved in methanol (50 ml)
- customprecipitated with ethyl acetate (300 ml)
- customThe solid was again recrystallized from a mixture of methanol and ethyl acetate
- washwashed with ethyl acetate (2×25 ml)
- customdried in an oven under high vacuum at 50° C. overnight
Sources & evidence
- ORD record
- ord-35379bfe34664ac48d3466f65a4d96bc
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06551831B2
Reaction notes
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