Chlorosuccinimide → 4-(4-Chloromethyl-5-methyl-1,3-thiazol-2-yl)morpholine

HRID 2221586Notes

Reaction equation

HRID 2221586 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[S:5][C:6]=1[CH3:7].[Cl:14]N1C(=O)CCC1=O>C(#N)C>[Cl:14][CH2:1][C:2]1[N:3]=[C:4]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 230765184-(4,5-Dimethyl-1,3-thiazol-2-yl)morpholine

Product 1

HCID 230763504-(4-Chloromethyl-5-methyl-1,3-thiazol-2-yl)morpholineYield 35.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(4,5-dimethyl-1,3-thiazol-2-yl)morpholine (5.0 g) in acetonitrile (100 mL) was added N-chlorosuccinimide (3.36 g) at room temperature, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 4-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl)morpholine as colorless crystals (2.06 g, 35%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 110-111° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added to the residue
  3. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-097fd716ebe04c199891b6912e1c5af2
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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