Hydrochloric Acid → 1-[4-Fluoro-2-(methylsulfanyl)phenyl]methanamine

HRID 1664179Notes

Reaction equation

HRID 1664179 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:10][CH3:11])[CH:3]=1.CO.Cl.O>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([S:10][CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 16753944410545-57-2

Product 1

HCID 167539431-[4-Fluoro-2-(methylsulfanyl)phenyl]methanamineYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4-Fluoro-2-(methylthio)benzonitrile (prepared as in Anthony, N. J. et al. PCT Appl. WO 02/30931, 2002) (1.67 g, 0.1 mol) was dissolved in 20 mL THF (under N2) and treated with 10 mL 2M BH3—(CH3)2S. This was heated at 60° C. for 2 hrs. Heating was discontinued and 5 mL MeOH was cautiously added, followed by the cautious addition of 4 mL 6N HCl. Then 20 mL more H2O added and EtOAc and the layers were separated. The aqueous layer was made basic with 1N NaOH and extracted with CH2Cl2. The extracts were dried (MgSO4), filtered, concentrated and dried in vacuum to give the title compound (1.3 g, 76%)as a solid. 1H NMR (500 MHz, CDCl3) δ: 7.20-7.31 (1 H, m) 6.90 (1H, dd, J=2.4 Hz) 6.75-6.86 (1H, m) 3.86 (2H, s) 2.47 (3H, s). LC/MS (M+H): 172.

Workup

  1. temperatureHeating
  2. customEtOAc and the layers were separated
  3. extractionextracted with CH2Cl2
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried in vacuum

Sources & evidence

ORD record
ord-616de8d0c2c540fab3ec09c9a77c9aca
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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