Ammonia → HCID 86629666, compound

HRID 911654Notes

Reaction equation

HRID 911654 reaction equation
S(Cl)(Cl)=O.[CH:5]1([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[S:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C([N:23](CC)CC)C.N>ClCCl.O>[CH:5]1([C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH2:23])=[S:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 178526130HCID 178526130, compound

Product 1

HCID 86629666HCID 86629666, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Add thionyl chloride (1.35 mL, 18.4 mmol) to a mixture of 4-cycloheptylthio-benzoic acid (984 mg, 3.93 mmol) in dichloromethane (15 mL) at 0° C. Heat the mixture to reflux for 1 h. Cool the mixture to room temperature and concentrate in vacuo. Dissolve the residue in dichloromethane (20 mL) and cool to 0° C. Add triethylamine (1.1 mL, 7.86 mmol) and bubble ammonia gas through the solution Warm the mixture to room temperature and stir for 1 h. Dilute with water (20 mL) and extract the aqueous phase with dichloromethane (3×20 mL). Wash the combined organic extracts with saturated aqueous NaHCO3 (20 mL). Dry the organic solution over Na2SO4, filter and concentrate in vacuo to provide the desired intermediate as an off-white solid (976 mg, 99%). MS (APCI) m/z: 250 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 1 h
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the residue in dichloromethane (20 mL)
  5. temperaturecool to 0° C
  6. temperatureWarm the mixture to room temperature
  7. extractionextract the aqueous phase with dichloromethane (3×20 mL)
  8. washWash the combined organic extracts with saturated aqueous NaHCO3 (20 mL)
  9. dry with materialDry the organic solution over Na2SO4
  10. filtrationfilter
  11. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e4229d6d7ce04aebaa93a3e73bff1862
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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