Ammonia → HCID 86711600, compound

HRID 527366Notes

Reaction equation

HRID 527366 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].O>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

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24386Thionyl ChlorideHCID 580227444-(Cyclopropylsulfanyl)benzoic acid

Product 1

HCID 86711600HCID 86711600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (340 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 dichloromethane (1.9 mL), and the mixture is heated at reflux for 30 min. All volatiles are removed under reduced pressure, and the residue is dissolved in chloroform (1.9 mL). Concentrated aqueous ammonia (28%, 770 μL, 9.8 mmol) is added and the mixture is stirred at room temperature for 1 h. Water is added and the phases are separated. The organic layer is concentrated under reduced pressure. Yield: 137 mg (72% of theory); ESI mass spectrum: [M+H]+=194; r.t. HPLC: 0.45 min (X011_S03).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 30 min
  3. customAll volatiles are removed under reduced pressure
  4. dissolutionthe residue is dissolved in chloroform (1.9 mL)
  5. customthe phases are separated
  6. concentrationThe organic layer is concentrated under reduced pressure
  7. customr.t
  8. custom0.45 min (X011_S03)

Sources & evidence

ORD record
ord-3b6786a9f00d4aa2b3d057f4fe418bf7
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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