N,N-Dimethylbenzylamine → HCID 15916783, compound

HRID 544583Notes

Reaction equation

HRID 544583 reaction equation
[CH3:1][CH:2]([S:4]Cl)[CH3:3].[O:6]1[CH2:10][CH2:9][NH:8][C:7]1=[O:11].CN(C)CC1C=CC=CC=1>ClC1C=CC=CC=1.CN(C)C=O>[CH3:1][CH:2]([S:4][N:8]1[CH2:9][CH2:10][O:6][C:7]1=[O:11])[CH3:3]

Participants

6

Reactant 3

HCID 7681N,N-DimethylbenzylamineHCID 739492-OxazolidinoneHCID 11116012HCID 11116012, compound

Product 1

HCID 15916783HCID 15916783, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7964ChlorobenzeneSolvent2×

Procedure

A solution of 0.6 mol of 2-propylsulphenyl chloride in 200 ml of chlorobenzene was added dropwise at 0° to 10° C. to 52.2 g (0.6 mol) of oxazolidin-2-one and 85 g (0.62 mol) of dimethylbenzylamine in 200 ml of chlorobenzene and 50 ml of dimethylformamide. After stirring for 1.5 hours at room temperature, the mother liquor was filtered from precipitated amine hydrochloride, washed with water and dried over sodium sulphate and the solvent was subsequently removed in vacuo at 40° C. 58 g of 3-(2-propylthio)oxazolidin-2-one were obtained as a brown oil.

Workup

  1. filtrationthe mother liquor was filtered
  2. customfrom precipitated amine hydrochloride
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent was subsequently removed in vacuo at 40° C

Sources & evidence

ORD record
ord-e428752b15074de886ae961dc7326d0e
Source dataset
uspto-grants-1984_05
Patent number
US04451475

Reaction notes

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