Thiomorpholine → HCID 86688897, compound

HRID 404637Notes

Reaction equation

HRID 404637 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(C(C)C)C(C)C.[NH:23]1[CH2:28][CH2:27][S:26][CH2:25][CH2:24]1>C(#N)C>[C:8]1([CH:2]([N:23]2[CH2:28][CH2:27][S:26][CH2:25][CH2:24]2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 67164ThiomorpholineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 86688897HCID 86688897, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol) was dissolved in acetonitrile (4.0 ml). DIPEA (0.26 ml, 1.481 mmol) and thiomorpholine (0.15 ml, 1.41 mmol) were sequentially added and the solution was stirred at room temperature for 1.5 hours. Acetonitrile was evaporated and the residue was purified by flash chromatography (petroleum ether/EtOAc=95/5) to obtain ethyl 2-phenyl-2-thiomorpholinoacetate (362 mg, quantitative yield) as a colorless oil.

Workup

  1. customAcetonitrile was evaporated
  2. customthe residue was purified by flash chromatography (petroleum ether/EtOAc=95/5)

Sources & evidence

ORD record
ord-ab62a2473b1041ffae859d6daacb56ae
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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