Ethyl Thioglycolate → HCID 53677012, compound

HRID 376974Notes

Reaction equation

HRID 376974 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:21])[C:12]([CH3:20])([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH3:13])=[CH:7][CH:6]=1.C([O:26][CH2:27][CH3:28])(=O)CS.O.C1(C)C=C[C:33]([S:36](O)(=O)=O)=CC=1.[OH-].[Na+]>>[CH3:20][C:12]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)([CH3:13])[C:11]([C:8]1[CH:9]=[CH:10][C:5]([S:4][CH2:3][CH2:2][O:1][C:27](=[O:26])[CH2:28][CH2:33][SH:36])=[CH:6][CH:7]=1)=[O:21]

Participants

5

Reactant 4

HCID 12185Ethyl ThioglycolateHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 18755078HCID 18755078, compound

Product 1

HCID 53677012HCID 53677012, compound

Conditions

Temperature
100 °C

Procedure

5.9 g (19.1 mmol) of 1-[4-(2-hydroxyethylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one, 4.2 ml (38.2 mmol) of ethyl thioglycolate, and 4.4 g (22.9 mmol) of p-toluenesulfonic acid monohydrate are mixed and stirred at 100° C. for 24 h. Then the solution is cooled to room temperature and neutralized with 1N NaOH. The crude product is extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate -hexane (30:70) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 1.99 (t, 1H), 2.57 (t, 4H), 3.22-3.30 (m, 4H), 3.70 (t, 4H), 4.36 (t, 2H), 7.34 (d, 2H), 8.51 (d, 2H).

Workup

  1. extractionThe crude product is extracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel with ethyl acetate -hexane (30:70) as an eluent

Sources & evidence

ORD record
ord-50924bbc24e049a9bf71de8de0ecbc5f
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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