Thiourea → HCID 86675111, compound

HRID 2400254Notes

Reaction equation

HRID 2400254 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[F:11].NC(N)=[S:14]>C(O)C>[F:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH2:2][SH:14])[C:7]#[N:8]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 27831494-(Bromomethyl)-3-fluorobenzonitrile

Product 1

HCID 86675111HCID 86675111, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromomethyl)-3-fluorobenzonitrile (0.8 g, 3.7 mmol) and thiourea (0.57 g, 7.4 mmol) in ethyl alcohol (EtOH; 20 mL) was heated to reflux for 1 h. The progress of the reaction was monitored by TLC; the reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was washed with EtOAc (50 mL), treated with 1.6 N NaOH and stirred for 20 h at RT. The reaction mixture was adjusted to pH˜4 with concentrated HCl and diluted with Et2O (50 mL). The organic layer was washed with H2O (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude I-2 (300 mg). The crude material was used without further purification. 1H NMR (500 MHz, CDCl3): δ 7.45 (dd, J=9.5 Hz, 1.5 Hz, 1H), 7.40-7.37 (m, 2H), 3.76 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with EtOAc (50 mL)
  5. additiontreated with 1.6 N NaOH
  6. additiondiluted with Et2O (50 mL)
  7. washThe organic layer was washed with H2O (25 mL) and brine (25 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto afford the crude I-2 (300 mg)
  11. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-60ba666888834dbfb4ea9e9c80bce2d9
Source dataset
uspto-grants-2014_08
Patent number
US08796001B2

Reaction notes

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