Hydrochloric Acid → 2-(1,3-Benzothiazol-2-yl)acetonitrile
Reaction equation
[CH2:1]([C:4]#[N:5])[C:2]#[N:3].C(O)C.Cl.N[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17]>C(Cl)(Cl)Cl>[S:17]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:3]=[C:2]1[CH2:1][C:4]#[N:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of malonodinitrile (13.22 g, 0.200 mole) in dry chloroform (100 mL) was added ethanol (9.2 g, 0.200 mole). Hydrogen chloride (8.0 g, 0.220 mole) was passed into the solution at room temperature and the resulting suspension was stirred for an additional 16 hours at room temperature. The excess of hydrogen chloride was removed by passing dry nitrogen into the reaction mixture. A solution of o-aminothiophenol (25 g, 0.200 mole) in chloroform was added to the reaction mixture dropwise during 30 min and the reaction mixture was stirred for 1 hour at 60° C. After that the reaction mixture was cooled to room temperature, washed with water (2×100 mL) and dried with magnesium sulfate. Chloroform was removed using a rotary evaporator. The solid residue was recrystallized from ethyl alcohol. White crystals. The yield was 26.1 g (75% of theory). Mp=101-103° C.
Workup
- customwas passed into the solution at room temperature
- customThe excess of hydrogen chloride was removed
- stirringthe reaction mixture was stirred for 1 hour at 60° C
- temperatureAfter that the reaction mixture was cooled to room temperature
- washwashed with water (2×100 mL)
- dry with materialdried with magnesium sulfate
- customChloroform was removed
- customa rotary evaporator
- customThe solid residue was recrystallized from ethyl alcohol
Sources & evidence
- ORD record
- ord-cdc4ba3541b0469686af654ff80cee83
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835632B2
Reaction notes
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