Hydrochloric Acid → 4-(3-nitrobenzoyl)thiomorpholine-3-carboxylic Acid Ethyl Ester

HRID 749096Notes

Reaction equation

HRID 749096 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][S:10][CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].CN(C1C=CC=CN=1)C.[N+:21]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28])([O-:23])=[O:22].Cl>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][S:10][CH2:9][CH2:8][N:7]1[C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8495Benzoyl chloride, 3-nitro-HCID 218852-DimethylaminopyridineHCID 13604869Ethyl thiomorpholine-3-carboxylate

Product 1

HCID 181465524-(3-nitrobenzoyl)thiomorpholine-3-carboxylic Acid Ethyl EsterYield 63.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of thiomorpholin-3-ylcarboxylic acid ethyl ester (5.05 g) in methylene chloride (120 mL) were added dimethylaminopyridine (352 mg), triethylamine (4.9 mL) and 3-nitrobenzoyl chloride (5.62 g) in ice bath and then the mixture was stirred at room temperature overnight. 2N hydrochloric acid was added to the reaction mixture, which was extracted with methylene chloride. The extract was wash with a saturated aqueous sodium hydrogen carbonate solution and brine sequentially, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give the title compound (5.91 g) having the following physical data.

Workup

  1. extractionwas extracted with methylene chloride
  2. washThe extract was wash with a saturated aqueous sodium hydrogen carbonate solution and brine sequentially
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2f67720ae1d74227841959fa414339a3
Source dataset
uspto-grants-2008_07
Patent number
US07402580B2

Reaction notes

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