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

HRID 2091787Notes

Reaction equation

HRID 2091787 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-00f84e51ad4e4a2fa539af01019251c6
Source dataset
uspto-grants-2013_05
Patent number
US08440657B2

Reaction notes

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