Thiourea → HCID 57827584, compound

HRID 1842181Notes

Reaction equation

HRID 1842181 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Cl[CH2:6][C:7]1[CH2:11][CH2:10][CH2:9][C:8]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18]>C(O)C>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C@:8]12[CH2:9][CH2:10][CH2:11][C@H:7]1[CH2:6][S:3][C:2]([NH2:4])=[N:1]2

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 57827260HCID 57827260, compound

Product 1

HCID 57827584HCID 57827584, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (2.60 g) was added to a solution of 1-(2-chloromethylcyclopent-1-enyl)-2-fluorobenzene obtained in Preparation Example 3-(4) (7.20 g) in ethanol (100 mL), and the mixture was stirred with heating under reflux for five hours. The reaction solution was cooled to room temperature and the solvent was evaporated under reduced pressure. The residual syrup was washed with heptane, followed by drying under reduced pressure. Trifluoroacetic acid (50.0 mL) and trifluoromethanesulfonic acid (10.0 mL) were added to the residue in an ice bath. Then, the reaction mixture was warmed to room temperature and stirred for four days. The reaction solution was poured into ice, diluted with ether and then neutralized with sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was purified by NH-silica gel column chromatography to obtain the title compound (4.98 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for five hours
  3. customthe solvent was evaporated under reduced pressure
  4. washThe residual syrup was washed with heptane
  5. customby drying under reduced pressure
  6. additionTrifluoroacetic acid (50.0 mL) and trifluoromethanesulfonic acid (10.0 mL) were added to the residue in an ice bath
  7. temperatureThen, the reaction mixture was warmed to room temperature
  8. stirringstirred for four days
  9. additionThe reaction solution was poured into ice
  10. additiondiluted with ether
  11. extractionfollowed by extraction with ethyl acetate
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. customThe drying agent was removed by filtration
  14. concentrationthe filtrate was concentrated under reduced pressure
  15. customto obtain a residue
  16. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-690b1b70d36d419c91f50345d7527272
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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