Potassium Hydroxide → HCID 21997643, compound
Reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[K+].IC[C:16]#[N:17]>O.C(O)(=O)C.C(O)C>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:4]=1[S:3][CH2:2][C:16]#[N:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 10 °C
Procedure
A suspension of 2-amino-6-fluoro-benzothiazole (5.13 g) was stirred for 6½ h at 165-170 ° C. under nitrogen in a solution of potassium hydroxide (10.3 g) in water (20 ml). The resulting mixture was cooled to 10° C. and adjusted to pH ˜8 by adding acetic acid, keeping the temperature below 25° C. The mixture was cooled to 10° C. and ethanol (30 ml) and iodoacetonitrile (2.20 ml) were added. After stirring for 15 min acetic acid (1.8 ml) was added and approx. half of the solvent was removed in vacuo. The residue was diluted with water (150 ml) and extracted with ethyl acetate (50 ml). The extract was dried over sodium sulfate, filtered and evaporated to give the title compound as a practically pure yellow oil. Yield 4.88 g (88%); 1H-NMR (DMSO-d6), δ (ppm): 7.26-7.14 (m, 1H, Ar—H), 7.09-6.95 (m, 1H, Ar—H), 6.85-6.72 (m, 1H, Ar—H), 5.36 (br, 2H, NH2), 3.99 (s, 2CH2).
Workup
- customthe temperature below 25° C
- temperatureThe mixture was cooled to 10° C.
- additionwas added
- customapprox. half of the solvent was removed in vacuo
- additionThe residue was diluted with water (150 ml)
- extractionextracted with ethyl acetate (50 ml)
- dry with materialThe extract was dried over sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-7d3374b0dd314dc8a498247276df9736
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06232310B1
Reaction notes
Loading…