Water → 4-Nitrophenyl thiomorpholine-4-carboxylate

HRID 220029Notes

Reaction equation

HRID 220029 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][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16].O>ClCCl.C(OCC)(=O)C>[N:1]1([C:15]([O:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[O:16])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67164ThiomorpholineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 581164954-Nitrophenyl thiomorpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.7 g (74.4 mmol) of thiomorpholine were initially charged in 100 ml of dichloromethane and, while cooling with an ice bath, admixed with 20.7 ml (15.1 g, 148.8 mmol) of triethylamine. 10.0 g (49.6 mmol) of 4-nitrophenyl chloroformate were added in portions. The reaction mixture was stirred at RT for one hour, and admixed with water and ethyl acetate. The organic phase was removed, washed with 1 N hydrochloric acid and saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 13.2 g (99% of theory)

Workup

  1. temperaturewhile cooling with an ice bath
  2. customThe organic phase was removed
  3. washwashed with 1 N hydrochloric acid and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e18799db951460d901d060ce46f666f
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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