Thionyl Chloride → HCID 58424863, compound

HRID 2409443Notes

Reaction equation

HRID 2409443 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:16])[N:8]([CH2:17][O:18][CH3:19])[C:7]=2[CH:20]=1.S(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:23][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:16])[N:8]([CH2:17][O:18][CH3:19])[C:7]=2[CH:20]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 58424836HCID 58424836, compound

Product 1

HCID 58424863HCID 58424863, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous dichloromethane (10 ml) was added to the compound (50.0 mg, 0.182 mmol) prepared in step 5, and thionyl chloride (0.016 ml, 0.219 mmol) was added dropwise at room temperature. The resulting mixture was stirred at room temperature for 2 hours and poured into sodium bicarbonate aqueous solution. The mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the title compound (51.4 mg, yield: 96%, white solid). The compound was used in the following reaction without further purification.

Workup

  1. additionwas added dropwise at room temperature
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7837c5e771b24544b74e044ff99c5cb6
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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