Hydrochloric Acid → HCID 11821636, compound

HRID 378344Notes

Reaction equation

HRID 378344 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]([O:17]C)=[O:16])[CH:9]=1)[C:3]([O:5]C)=O.[NH2:19][C:20](N)=[S:21].Cl.C([OH:26])C>>[O:26]=[C:20]1[NH:19][C:3](=[O:5])[CH:2]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH:9]=2)[C:15]([OH:17])=[O:16])[S:21]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2723790ThioureaHCID 11782148HCID 11782148, compound

Product 1

HCID 11821636HCID 11821636, compoundYield 39%

Procedure

To a solution of methyl 2-bromo-3-(3-methoxycarbonyl-4-fluorophenyl)propionate (1.22 g) in ethanol (40 ml), thiourea (356 mg) was added and the mixture was refluxed for 11 hours under heat. After cooling, this was concentrated under reduced pressure and water (50 ml) was added to the residue. After pH was adjusted to around 8 with saturated aqueous solution of sodium bicarbonate under stirring, ether (20 ml) and n-hexane (40 ml) were added, which was stirred for 10 minutes as it was. The crystals were collected by filtration, washed with water, and then dried. The solids thus obtained were dissolved into sulforane (10 ml) and, after 6N hydrochloric acid (20 ml) was added, the mixture was refluxed for 8 hours under heat. After cooling, this was poured into ice water and the crystals deposited were collected by filtration, washed with water, and then dried to obtain 403 mg (39%) of aimed compound as crystals.

Workup

  1. temperaturethe mixture was refluxed for 11 hours
  2. temperatureunder heat
  3. temperatureAfter cooling
  4. concentrationthis was concentrated under reduced pressure and water (50 ml)
  5. additionwas added to the residue
  6. additionether (20 ml) and n-hexane (40 ml) were added
  7. stirringwhich was stirred for 10 minutes as it
  8. filtrationThe crystals were collected by filtration
  9. washwashed with water
  10. customdried
  11. customThe solids thus obtained
  12. dissolutionwere dissolved into sulforane (10 ml)
  13. temperaturethe mixture was refluxed for 8 hours
  14. temperatureunder heat
  15. temperatureAfter cooling
  16. filtrationthe crystals deposited were collected by filtration
  17. washwashed with water
  18. customdried

Sources & evidence

ORD record
ord-0f047e95a6c0402d83e667a28b4082be
Source dataset
uspto-grants-2000_02
Patent number
US06030990

Reaction notes

Loading…