Thionyl Chloride → HCID 16111878, compound

HRID 252841Notes

Reaction equation

HRID 252841 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:21])=O>CN(C)C=O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([Cl:21])=[O:15])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 65042324-[2-(Morpholin-4-yl)ethoxy]benzoic acid

Product 1

HCID 16111878HCID 16111878, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
80 °C

Procedure

4-(2-Morpholinoethoxy)benzoic acid 194 (330 mg, 1.31 mmol) was dissolved in thionyl chloride (4 mL) and a few drops of dimethylformamide were added. The reaction mixture was allowed to stir at 80° C. in a sealed tube for 1.5 hrs then opened to leave evaporate overnight. The residue was placed on a vacuum pump overnight and used as is in the next reaction (0.30 g, 100%). MS: 269.08 (calc, COCl), 265.13 (calc, Me ester), 266.2 (obs, Me ester)

Workup

  1. customto leave
  2. customevaporate overnight
  3. customwas placed on a vacuum pump overnight
  4. customas is in the next reaction (0.30 g, 100%)

Sources & evidence

ORD record
ord-848074dd8f4d4b8d878ab6ea88a4bd53
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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