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Hydrochloric Acid → (+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

HRID 398814
Notes
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Reaction equation

HRID 398814 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:12]([C:14]1([CH2:20][OH:21])[CH2:18][O:17][C:16](=[O:19])[NH:15]1)[CH3:13].Cl>N1C=CC=CC=1.[Cl-].[Na+].O>[CH2:12]([C:14]1([CH2:20][O:21][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH2:18][O:17][C:16](=[O:19])[NH:15]1)[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 112635594-Ethyl-4-hydroxymethyl-2-oxazolidinone

Product 1

HCID 18968885(+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinoneYield 91.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 57417360
Sodium chloride; water
Solvent

Procedure

Tosyl chloride (142.2 g, Aldrich) was added to an ice-chilled solution of the product from step (a) (102.7 g) dissolved in pyridine (175 ml. Aldrich). The reaction mixture was stirred at ice bath temperature for six hours, then allowed to come to room temperature. The heterogeneous mixture was added to 1500 ml of a solution of brine and 1N HCl. stirred until solids appeared, filtered and washed with diethyl ether to give 194.6 g of a beige solid as the title product. 1H NMR consistent with the proposed structure.

Workup

  1. customto come to room temperature
  2. stirringstirred until solids
  3. filtrationfiltered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a8e6bcee15234267afc3ea6001613b81
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05817652

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes