Methanethiol → HCID 15457081, compound

HRID 1385947Notes

Reaction equation

HRID 1385947 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]2[C:11]([Cl:12])=[CH:10][C:9]([F:13])=[C:8]([C:14]3[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[C:6]=2[CH:7]=1.[CH3:26][SH:27].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:12][C:11]1[C:5]2[O:4][C:3]([CH2:2][S:27][CH3:26])=[CH:7][C:6]=2[C:8]([C:14]2[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:21])([F:23])[F:22])=[CH:18][CH:19]=2)=[C:9]([F:13])[CH:10]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 11430Potassium CarbonateHCID 15457079HCID 15457079, compound

Product 1

HCID 15457081HCID 15457081, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.31 g (0.71 mmol) of 3-(2-bromomethyl-7-chloro-5-fluorobenzofuran-4-yl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 20 ml of THF, and 0.014 g (0.85 mmol) of a methanethiol 30% methanol solution and 0.12 g (0.85 mmol) of potassium carbonate were added thereto, followed by stirring at room temperature for 8 hours. THF was distilled off under reduced pressure. Then, the obtained residue was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. Then, the obtained crude crystals were washed with n-hexane to obtain 0.28 g (yield: 98%) of the desired product. 1H-NMR (300 MHz, CDCl3) δ value: 2.17(3H,s), 3.73(3H,s), 3.79(2H,s), 6.47(1H,s), 6.80(1H,d), 7.14(1H,d), 7.54(1H,d)ppm.

Workup

  1. distillationTHF was distilled off under reduced pressure
  2. additionThen, the obtained residue was poured into water
  3. extractionextracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customThen, the obtained crude crystals
  8. washwere washed with n-hexane

Sources & evidence

ORD record
ord-95be9f5643ce43478d333d3945b62e27
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

Loading…