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

HRID 661211
Notes
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Reaction equation

HRID 661211 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent
HCID 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-edfb7684095f41238879b4e88c772304
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084469B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes