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

HRID 1726592Notes

Reaction equation

HRID 1726592 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.S(C)C.CO.Cl>O1CCCC1.C(OCC)(=O)C.O>[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1068Dimethyl SulfideHCID 16753944410545-57-2

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Under N2, 4-fluoro-2-(methylthio)benzonitrile (1.67 g, 0.1 mol) was dissolved in 20 mL tetrahydrofuran and treated with 10 mL 2M BH3.Me2S. 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. Additional H2O (20 mL) was added followed by ethyl acetate. 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 vacuo to give 1.3 g of the title compound as a solid (Yield 76%). 1H NMR (500 MHz, CDCl3) δ ppm: 7.20-7.31 (1H, 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/z 172.

Workup

  1. additiontreated with 10 mL 2M BH3
  2. temperatureHeating
  3. customThe layers were separated
  4. extractionextracted with CH2Cl2
  5. dry with materialThe extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-cdf319fedf5148a495c1ad374614e1b9
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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