Water → 4-Nitrophenyl thiomorpholine-4-carboxylate 1,1-dioxide

HRID 220055Notes

Reaction equation

HRID 220055 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][S:5](=[O:9])(=[O:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19].O>ClCCl.C(OCC)(=O)C>[N:2]1([C:18]([O:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:19])[CH2:7][CH2:6][S:5](=[O:9])(=[O:8])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 12324096Thiomorpholine 1,1-dioxide hydrochloride

Product 1

HCID 581165414-Nitrophenyl thiomorpholine-4-carboxylate 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

17.0 g (99.2 mmol) of thiomorpholine 1,1-dioxide hydrochloride 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 30 minutes, admixed with water and ethyl acetate and then filtered. The residue was dried under high vacuum. Yield: 12.4 g (83% of theory)

Workup

  1. temperaturewhile cooling with an ice bath
  2. filtrationfiltered
  3. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-afc8319216b54771bfc39a25664dbb30
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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