2-Aminothiophenol → 4-(1,3-benzothiazol-2-yl)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18]>CS(C)=O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]2[S:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)=[CH:5][CH:4]=1)#[N:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
44.6 g (0.34 mol) of 4-cyanobenzaldehyde and 54.4 g (0.64 mol) of o-aminobenzenethiol were dissolved in 300 ml of dimethyl sulfoxide, and the temperature of the solution was raised to 140° C. The produced water and the dimethyl sulfoxide were distilled off. After heating for one hr. the residue was cooled, water was added thereto, and the resultant precipitate was collected by filtration and washed with ethanol. The crude crystal thus obtained was recrystallized from ethyl acetate to give 2-(4'-cyanophenyl)benzothiazole. 22.4 g (0.095 mol) of the compound was dissolved in 250 ml of acetic acid, and 18.6 g (0.116 mol) of bromine was dropwise added thereto. As soon as bromine was added, a yellow bromine adduct was produced. Subsequently, 150 ml of water was added, and the mixture was stirred at 80° C. for 2 hr. It was then cooled, and the resultant precipitate was collected by filtration and washed with ethanol. The crude product thus obtained was recrystallized from ethyl acetate.
Workup
- distillationThe produced water and the dimethyl sulfoxide were distilled off
- temperatureAfter heating for one hr
- temperaturethe residue was cooled
- additionwater was added
- filtrationthe resultant precipitate was collected by filtration
- washwashed with ethanol
- customThe crude crystal thus obtained
- customwas recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-b3cbd3555ed04d62b35358e32a110353
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05980779
Reaction notes
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