Ammonia → HCID 86711600, compound

HRID 524347Notes

Reaction equation

HRID 524347 reaction equation
S(Cl)(Cl)=O.[CH:5]1([S:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)[CH2:7][CH2:6]1.[NH3:18]>ClCCl>[CH:5]1([S:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:18])=[O:14])=[CH:11][CH:10]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 580227444-(Cyclopropylsulfanyl)benzoic acid

Product 1

HCID 86711600HCID 86711600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionylchloride (342 μL, 4.7 mmol) is added to a solution of 4-cyclopropylsulfanyl-benzoic acid (prepared as described in WO07003960, 190 mg, 0.98 mmol) in dichloro-methane (1.9 mL). The mixture is heated at reflux for 30 min and concentrated under reduced pressure. The residue is treated with toluene, and all volatiles are evaporated. The residue is dissolved in chloroform (1.9 mL) and treated with concentrated aqueous ammonia (770 μL, 9.8 mmol). The mixture is stirred at room temperature for 1 h and then extracted with water. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. Yield: 137 mg (72% of theory); ESI mass spectrum: [M+H]+=194; Retention time HPLC: 0.45 min (X011_S03).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 30 min
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue is treated with toluene
  5. customall volatiles are evaporated
  6. dissolutionThe residue is dissolved in chloroform (1.9 mL)
  7. extractionextracted with water
  8. dry with materialThe organic layer is dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. custom0.45 min (X011_S03)

Sources & evidence

ORD record
ord-ac918964e5eb48abb0f8e35f6aae8456
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

Loading…