Triethylamine → 3-fluoro-2-methylphenylisothiocyanate
Reaction equation
[CH3:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]=[C:10]=[S:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a solution of 2-methyl-3-fluoroaniline (1.0 g, 8.0 mmol) in 30 mL of toluene at room temperature, thiophosgene (0.94 mL, 12 mmol) and triethylamine (1.34 mL, 12 mmol) was added. The mixture was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The combined organic layer was then concentrated to give the desired product (1.1 g, 82%). EI-MS m/z 168.2 (M+).
Workup
- customThe mixture was partitioned between ethyl acetate and water
- concentrationThe combined organic layer was then concentrated
Sources & evidence
- ORD record
- ord-29631824a64d4a1494f487d135d9e8d5
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680317B2
Reaction notes
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