Morpholine → 4-[4-(Methylthio)benzoyl]morpholine

HRID 268601

Reaction equation

HRID 268601 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.Cl.CN(C)CCN=C=NCC.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1COCC1>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:9])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 832304-(Methylthio)benzoic acidHCID 57494384N-[2-(dimethylamino)ethyl]-N'-ethylcarbodiimide hydrochloride

Product 1

HCID 255722614-[4-(Methylthio)benzoyl]morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(methylthio)benzoic acid (6.76 g, 40.2 mmol) and N-[2-(dimethylamino)ethyl]-N′-ethylcarbodiimide hydrochloride (9.24 g, 48.2 mmol) in THF (100 mL) was added morpholine (4.2 mL, 48.2 mmol). After stirring for 2 hours, the reaction was concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and 2M hydrochloric acid (150 mL). The organic phase was separated, washed with 1M aqueous sodium carbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound LC retention time 3.52 mins MS m/z 238 (MH+).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate (100 mL) and 2M hydrochloric acid (150 mL)
  3. customThe organic phase was separated
  4. washwashed with 1M aqueous sodium carbonate solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-037be1b1b0ef41ba93b21ed6ef1338dd
Source dataset
uspto-grants-2008_11
Patent number
US07446117B2

Linked notes

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