Triethylamine → HCID 21836543, compound

HRID 1739750Notes

Reaction equation

HRID 1739750 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>ClCCl>[CH2:18]([O:17][C:15]([N:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 67164Thiomorpholine

Product 1

HCID 21836543HCID 21836543, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thiomorpholine (5 g, 1 mol. equiv.) and triethylamine (5.4 g, 1.1 mol. equiv.) in dichloromethane (200 ml) at 0° C. under nitrogen was slowly added benzyl chloroformate (8.68 g, 1.05 mol. equiv.) over fifteen minutes. The reaction was then allowed to warm to room temperature and stirred for a further sixteen hours. The reaction was washed with a saturated aqueous sodium bicarbonate solution. The organic layer was dried using magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane to give the title compound (10 g). TLC=Rf 0.3 (silica, dichloromethane). Found: C, 59.24; H, 6.49; N, 5.78. C12H15NO2S requires C, 59.12; H, 6.23: N, 5.70%.

Workup

  1. customat 0° C.
  2. customover fifteen minutes
  3. washThe reaction was washed with a saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-db2acda861e144ad9cb5a591a51fb5ff
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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