Thiourea → HCID 23109614, compound

HRID 968975Notes

Reaction equation

HRID 968975 reaction equation
ClCC([NH:5][C:6]([CH3:17])([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([F:15])[CH:9]=1)=O.NC(N)=S>C(O)(=O)C.C(O)C>[F:15][C:10]1[CH:9]=[C:8]([CH2:7][C:6]([NH2:5])([CH3:16])[CH3:17])[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 23109632HCID 23109632, compound

Product 1

HCID 23109614HCID 23109614, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-N-[1-(3-fluoro-4-methylphenyl)-2-methylpropan-2-yl]acetamide (131.6 g) obtained in Step 6 was dissolved in acetic acid (200 ml) and ethanol (1 L), and thiourea (46.6 g) was added. The mixture was stirred overnight at 100° C. The reaction mixture was cooled to room temperature, and the precipitated crystals were filtered. The filtrate was concentrated under reduced pressure, and 4N-sodium hydroxide solution (300 ml) was added to the obtained residue. The mixture was extracted 3 times with toluene. The organic layer was washed with brine, and concentrated under reduced pressure. The obtained residue was dissolved in diethyl ether (1 L) and 4N-hydrochloric acid/ethyl acetate solution (255 ml) was added dropwise under ice-cooling. The mixture was stirred for 1 hr and the precipitated crystals were collected by filtration. The obtained crystals were added to a mixture of toluene and 4N-aqueous sodium hydroxide solution. The toluene layer was separated, washed twice with water, and concentrated under reduced pressure to give the title compound (57.9 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitated crystals were filtered
  3. concentrationThe filtrate was concentrated under reduced pressure, and 4N-sodium hydroxide solution (300 ml)
  4. additionwas added to the obtained residue
  5. extractionThe mixture was extracted 3 times with toluene
  6. washThe organic layer was washed with brine
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in diethyl ether (1 L)
  9. addition4N-hydrochloric acid/ethyl acetate solution (255 ml) was added dropwise under ice-
  10. temperaturecooling
  11. stirringThe mixture was stirred for 1 hr
  12. filtrationthe precipitated crystals were collected by filtration
  13. additionThe obtained crystals were added to a mixture of toluene and 4N-aqueous sodium hydroxide solution
  14. customThe toluene layer was separated
  15. washwashed twice with water
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ea0f2393a0043638601133c6d597b56
Source dataset
uspto-grants-2007_12
Patent number
US07304174B2

Reaction notes

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