Sodium Hydroxide → 3-Chloro-4-[(2-chloropyrimidin-4-yl)thio]-2-methylaniline
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#[N:10])=[C:4]([Cl:11])[C:3]=1[CH3:12].O.[SH-].[Na+].[BH4-].[Na+].[OH-].[Na+].[Cl:20][C:21]1N=C(Cl)[CH:24]=[CH:23][N:22]=1>CO.O>[Cl:11][C:4]1[C:3]([CH3:12])=[C:2]([CH:7]=[CH:6][C:5]=1[S:8][C:9]1[CH:24]=[CH:23][N:22]=[C:21]([Cl:20])[N:10]=1)[NH2:1]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Crude 4-amino-2-chloro-3-methylphenyl thiocyanate (600 mg, 3.0 mmol) was dissolved in a mixture of methanol:water (2:1, 22 mL) and cooled to 0° C. Sodium hydrosulfide monohydrate (338 mg, 4.6 mmol) and sodium borohydride (447 mg, 11.8 mmol) were added then the mixture was allowed to warm to room temperature and stir overnight. After this time sodium hydroxide (96 mg, 2 4 mmol) was added followed by 2,4-dichloropyrimidine (360 mg, 2 4 mmol) and the mixture allowed to stir for a further 24h. The methanol was removed in vacuo and then the mixture was extracted with ethyl acetate. The extracts were dried (Na2SO4) and evaporated then the residue was purified by flash chromatography to afford 3-chloro-4-[(2-chloropyrimidin-4-yl)thio]-2-methylaniline (353 mg, 41%).
Workup
- temperatureto warm to room temperature
- stirringto stir for a further 24h
- customThe methanol was removed in vacuo
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extracts were dried (Na2SO4)
- customevaporated
- customthe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-bdf6316b2b9347548381cd6d76757d55
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040549B2
Reaction notes
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