Hydrochloric Acid → 7-Fluoro-1,3-benzothiazol-2-amine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[S:11][C:12]#[N:13].C(O)C.Cl>O>[F:1][C:2]1[C:3]2[S:11][C:12]([NH2:13])=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-fluoro-3-nitro-2-thiocyanatobenzene 2 (3.96 g, 0.02 mol), ethanol (30 mL), water (25 mL) and conc. hydrochloric acid (25 mL) was refluxed gently during the addition of hydrogen-reduced iron powder (8 g). After refluxing for 16 hr, the liquor was filtered hot, cooled, the residue filtered, dissolved in hot water, and neutralized with ammonia and then extracted with EtOAc to get the compound 7-fluorobenzo[d]thiazol-2-amine (1 g) as a colorless oil. LC-MS: m/z 169.2 (M+H)+
Workup
- temperatureAfter refluxing for 16 hr
- filtrationthe liquor was filtered hot
- temperaturecooled
- filtrationthe residue filtered
- dissolutiondissolved in hot water
- extractionextracted with EtOAc
Sources & evidence
- ORD record
- ord-9ea32e9d4cb2489ea1c7a9824bd613c8
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365545B2
Reaction notes
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