Sodium methanethiolate → HCID 135743670, compound
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][N:16]=[N:15][C:14]=1[CH3:19].C[S-].[Na+]>CN(C)C=O>[CH3:19][C:14]1[N:15]=[N:16][CH:17]=[CH:18][C:13]=1[C:4]1[CH:5]=[C:6]([C:9]([F:11])([F:10])[F:12])[CH:7]=[CH:8][C:3]=1[OH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 4-[2-methoxy-5-(trifluoromethyl)phenyl]-3-methylpyridazine (Preparation 43, 650 mg, 2.4 mmol) in N,N-dimethylformamide (18 mL) was added sodium thiomethoxide (850 mg, 12 mmol) and reaction mixture was heated to 70° C. for 4 hours. The reaction mixture was then cooled to 0° C., poured onto ice water (50 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were washed with water (5×100 mL) and saturated aqueous sodium chloride solution (100 mL) then dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (20% ethyl acetate in heptane elution) to afford the title compound as a yellow solid (325 mg).
Workup
- temperatureThe reaction mixture was then cooled to 0° C.
- additionpoured onto ice water (50 mL)
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined organics were washed with water (5×100 mL) and saturated aqueous sodium chloride solution (100 mL)
- dry with materialthen dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude material was purified by silica gel column chromatography (20% ethyl acetate in heptane elution)
Sources & evidence
- ORD record
- ord-e6ed0497463f4de6a60bdde83cf049bb
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145407B2
Reaction notes
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