Hydrochloric Acid → 2-Amino-4-fluorobenzene-1-thiol
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9]C(C)=[N:7][C:6]=2[CH:11]=1.Cl>C(O)CO.[OH-].[Na+]>[NH2:7][C:6]1[CH:11]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[SH:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 129 °C
Procedure
A solution of 5-fluoro-2-methylbenzo[d]thiazole (1.2 g, 7.18 mmol) in ethylene glycol and NaOH (5N, 2 ml) was degassed under N2 for 10 min, then refluxed at 129° C. for 3 hours. The solution was cooled to 0° C. and then acidified to pH 3˜4 using c. HCl. The mixture was extracted with EtOAc (2×50 ml). The organic layer was washed with brine and dried with Na2SO4 and concentrated in vacuo. The crude residue (1.01 g, 98%) was used directly in the next step without purification.
Workup
- temperatureThe solution was cooled to 0° C.
- extractionThe mixture was extracted with EtOAc (2×50 ml)
- washThe organic layer was washed with brine
- dry with materialdried with Na2SO4
- concentrationconcentrated in vacuo
- customThe crude residue (1.01 g, 98%) was used directly in the next step without purification
Sources & evidence
- ORD record
- ord-38e9a4925477471da7fb67a13f1514d8
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822530B2
Reaction notes
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