Chlorosuccinimide → HCID 25027605, compound

HRID 1436460Notes

Reaction equation

HRID 1436460 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[N:12]=1.[Cl:24]N1C(=O)CCC1=O>CN(C)C=O>[Cl:24][C:10]1[S:9][C:8]([N:3]2[C:2]([CH3:23])([CH3:1])[CH2:6][O:5][C:4]2=[O:7])=[N:12][C:11]=1[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 25027135HCID 25027135, compound

Product 1

HCID 25027605HCID 25027605, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-[2-(4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzoate, prepared in Example 129, and N-chlorosuccinimide are combined in dimethylformamide (5 mL). The mixture is stirred for 5 days and partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated onto silica gel. The residue is purified by silica gel Flash Chromatography to give the title compound. The melting point is anticipated to be 152-155° C.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. concentrationconcentrated onto silica gel
  4. customThe residue is purified by silica gel Flash Chromatography

Sources & evidence

ORD record
ord-ba50093e5ecd4b00b4d8efe48bd816d4
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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