Ammonia → HCID 18187171, compound

HRID 1357734Notes

Reaction equation

HRID 1357734 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[CH2:11]1[C:17](=O)[CH2:16][S:13](=O)(=O)[CH2:12]1.[NH3:19].Cl>C(O)C.CCOCC>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]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:8]=[CH:9][CH:10]=1)#[N:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 90670m-FormylbenzonitrileHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxide

Product 1

HCID 18187171HCID 18187171, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

3-Cyanobenzaldehyde (132 mg, 1.01 mmol), tetrahydrothiophene-3-oxo-1,1-dioxide (272 mg, 2.03 mmol) and 2.0 M NH3 in ethanol (0.75 mL, 1.5 mmol) were heated to 80° C. in ethanol (4 mL) in a sealed tube for 3 days, cooled, treated with 1.0 M HCl in ether (1 mL), heated to reflux for 1 hour, cooled and solvent evaporated. The crude was flash chromatographed over silica gel (15% methanol/chloroform), and the product triturated with ethyl acetate to provide 87 mg of the title compound as an off-white solid.

Workup

  1. temperaturecooled
  2. temperatureheated
  3. temperatureto reflux for 1 hour
  4. temperaturecooled
  5. customsolvent evaporated
  6. customchromatographed over silica gel (15% methanol/chloroform)
  7. customthe product triturated with ethyl acetate

Sources & evidence

ORD record
ord-639a0904ac254514ad7ff18045a9681f
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

Loading…