Chlorine → 7-Chloro-1,3-benzothiazol-6-amine
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.[Cl:11]Cl.CCOC(C)=O.CCCCCC>CC(O)=O.CCOC(C)=O>[Cl:11][C:3]1[C:4]2[S:8][CH:7]=[N:6][C:5]=2[CH:9]=[CH:10][C:2]=1[NH2:1]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 6-aminobenzothiazole (2.0 g, 13.4 mmol) in 100 mL of AcOH was added a solution of Cl2 saturated AcOH and the resulting reaction mixture was stirred for 1 h at 25° C. Reaction mixture was concentrated in vacuo, yielding a yellow solid which was dissolved in EtOAc and washed with aq. NaHCO3. Organic layer was dried over is Na2SO4 and concentrated in vacuo, yielding an oil which was subjected to column chromatography (10-50% EtOAc/n-Hexane) to obtain 7.8 g (34 mmol, 80% ) of the desired product.
Workup
- customthe resulting reaction mixture
- customReaction mixture
- concentrationwas concentrated in vacuo
- customyielding a yellow solid which
- washwashed with aq. NaHCO3
- customOrganic layer was dried
- concentrationconcentrated in vacuo
- customyielding an oil which
Sources & evidence
- ORD record
- ord-f383dc6a7a1d496784762c99b8478ae3
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06159998
Reaction notes
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