Ammonia → 8-(3-Bromo-4-fluorophenyl)-2,3,4,5,6,8-hexahydrodithieno [3.2-b:2',3'-e]pyridine

HRID 1357732Notes

Reaction equation

HRID 1357732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[CH2:11]1[C:17](=O)[CH2:16][S:13](=O)(=O)[CH2:12]1.[NH3:19]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:12]3[S:13][CH2:16][CH2:17][C:11]=3[NH:19][C:17]3[CH2:11][CH2:12][S:13][C:16]2=3)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxide

Product 1

HCID 181870818-(3-Bromo-4-fluorophenyl)-2,3,4,5,6,8-hexahydrodithieno [3.2-b:2',3'-e]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Bromo-4-fluorobenzaldehyde (305 mg, 1.5 mmol), tetrahydrothiophene-3-oxo-1,1-dioxide (402 mg, 3.00 mmol), and 2.0 M NH3 in ethanol (1,1 mL, 2.2 mmol) in ethanol (3 mL) were heated to 80° C. for 3 days in a sealed tube, cooled, the solid precipitate collected, and washed with ethanol. The solid was heated to reflux overnight in ethanol with 1.0 M HCl in ether (1 mL), cooled, the solid collected, washed with ethanol and dried to provide 185 mg of the title compound as an off-white solid.

Workup

  1. temperaturecooled
  2. customthe solid precipitate collected
  3. washwashed with ethanol
  4. temperatureThe solid was heated
  5. temperatureto reflux overnight in ethanol with 1.0 M HCl in ether (1 mL)
  6. temperaturecooled
  7. customthe solid collected
  8. washwashed with ethanol
  9. customdried

Sources & evidence

ORD record
ord-b2f0dcc872f347a0913aee7f04b834bd
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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