Water → HCID 23076433, compound

HRID 2221648Notes

Reaction equation

HRID 2221648 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[N:11]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[S:13][C:14]=1[CH3:15].O>C(#N)C>[Cl:1][CH2:9][C:10]1[N:11]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[S:13][C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 23076440HCID 23076440, compound

Product 1

HCID 23076433HCID 23076433, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

N-Chlorosuccinimide (4.5 g) was added to a solution (100 ml) of tert-butyl 4-(4,5-dimethyl-1,3-thiazol-2-yl)piperazine-1-carboxylate (10 g) in acetonitrile at 0° C., and the mixture was stirred at 0° C. for 30 min. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (0:1-1:4-1:2, v/v) to give tert-butyl 4-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl)piperazine-1-carboxylate as colorless crystals (6.2 g, yield 55%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. washeluted with ethyl acetate-hexane (0:1-1:4-1:2

Sources & evidence

ORD record
ord-93e1e84bf7174080ac67b4b4420753d5
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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