Sodium hydride → 5-Bromo-6-fluorobenzo[d]thiazol-2-amine
Reaction equation
[Br:1][C:2]1[C:3]([F:13])=[CH:4][C:5](F)=[C:6]([NH:8][C:9]([NH2:11])=[S:10])[CH:7]=1.[H-].[Na+]>CN1C(=O)CCC1>[Br:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[S:10][C:9]([NH2:11])=[N:8][C:6]=2[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a solution of (5-Bromo-2,4-difluoro-phenyl)-thiourea (0.75 g, 2.80 mmol) in NMP (5.0 mL) was added NaH (0.17 g, 4.21 mmol, 60% dispersion in oil) portion wise. The reaction mixture was then heated at 130° C. for 2 h. The reaction mixture was then poured onto crushed ice and extracted with EtOAc (3×50 mL). The combined organics was evaporated to get the crude residue that was purified over silica gel (100-200 M, 12% EtOAc-Hexane) to obtain the desired compound (0.36 g, 52%). 1H-NMR (400 MHz, DMSO-d6): δ 7.57 (d, J=6.40 Hz, 1H), 7.66 (br s, 2H) and 7.79 (d, 8.80 Hz, 1H).
Workup
- additionThe reaction mixture was then poured
- customonto crushed ice
- extractionextracted with EtOAc (3×50 mL)
- customThe combined organics was evaporated
- customto get the crude residue that
- customwas purified over silica gel (100-200 M, 12% EtOAc-Hexane)
Sources & evidence
- ORD record
- ord-6098fcab77a7446b9265eec6b53918d6
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299065B2
Reaction notes
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