Ammonia → 3-Fluoro-4-(3,6-dihydro-2h-thiopyran-4-yl)benzenamine

HRID 723811Notes

Reaction equation

HRID 723811 reaction equation
O[C:2]1([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[F:15])[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.Cl.O.N>C(O)(=O)C>[F:15][C:9]1[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:8]=1[C:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 114815653-Fluoro-4-[4-(hydroxy)tetrahydrothiopyran-4-yl]benzenamine

Product 1

HCID 112295653-Fluoro-4-(3,6-dihydro-2h-thiopyran-4-yl)benzenamineYield 95.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Hydroxy-4-(2-fluoro-4-aminophenyl)tetrahydrothiopyran (11.35 g, 50 mM) and butylated hydroxytoluene (50 mg) as antioxidant were suspended in a mixture of concentrated hydrochloric acid (37%, 200 ml) and water (50 ml), and stirred at 80° under nitrogen for 18 hours. Glacial acetic acid (150 ml) was added, and reaction continued at 80° for a further 5 hours. After cooling, the reaction was made basic by the cautious addition of concentrated ammonia and ice. The mixture was extracted with diethyl ether (400 ml), the extract washed with water (100 ml), brine (100 ml), dried (magnesium sulfate), filtered and evaporated to give the title product (10 g) as a dark oil.

Workup

  1. customreaction
  2. waitcontinued at 80° for a further 5 hours
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with diethyl ether (400 ml)
  5. washthe extract washed with water (100 ml), brine (100 ml)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e0b3cf87642a48a498c1825a43578f1b
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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