Hydrochloric Acid → HCID 21836543, compound

HRID 860493Notes

Reaction equation

HRID 860493 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[CH:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15](Cl)=[O:16])=[CH:9][CH:8]=1.Cl>[OH-].[Na+]>[N:1]1([C:15]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=2)=[O:16])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 67164Thiomorpholine

Product 1

HCID 21836543HCID 21836543, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of thiomorpholine (2 g) in 1N NaOH (11.6 mL) was added benzyl chloridocarbonate (1.66 mL) under ice water cooling and the mixture was stirred at ambient temperature for 2 hours. The solution was neutrolized with 1N HCl and extracted with EtOAc twice. The combined organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography to give benzyl 4-thiomorpholinecarboxylate as a colorless solid (4.8 g).

Workup

  1. extractionextracted with EtOAc twice
  2. washThe combined organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-afb98021ad1a4fd0aa46b1e5d9942440
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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