Water → HCID 22726929, compound

HRID 2085980Notes

Reaction equation

HRID 2085980 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1[S:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12].[Cl:20]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:20][C:5]1[S:6][C:7]([S:8][CH2:9][CH2:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:3]([CH2:2][Cl:1])[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 22726957HCID 22726957, compound

Product 1

HCID 22726929HCID 22726929, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloromethyl-5-(2-phenylsulfonylethyl)thio-1,3-thiazole (400 mg, 1.2 mmol) in N,N-dimethylformamide (3 mL) was added N-chlorosuccinimide (160 mg, 1.2 mmol), and the mixture was stirred at room temperature for 16 h. The resulting mixture was poured into water and extracted with ethyl acetate. The organic solution was washed with water, dried over sodium sulfate, and concentrated; The residue was chromatographed (silica gel, 20% ethyl acetate-hexane), affording 260 mg of the title compound. 1H NMR (CDCl3) δ 3.09 (2H), 3.36 (2H), 4.60 (2H), 7.5-7.9 (5H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed (silica gel, 20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-a826fe7bc65143209bae6b573f9b3f43
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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