Thionyl Chloride → HCID 22726957, compound

HRID 378524Notes

Reaction equation

HRID 378524 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:8]=[CH:9][S:10][C:11]=1[S:12][CH2:13][CH2:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16]>CN(C)C=O>[Cl:3][CH2:6][C:7]1[N:8]=[CH:9][S:10][C:11]=1[S:12][CH2:13][CH2:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15885282HCID 15885282, compound

Product 1

HCID 22726957HCID 22726957, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Thionyl chloride (1.5 mL) was mixed with N,N-dimethylformamide (15 mL) and stirred at room temperature for 30 min. The resulting solution was then transferred via syringe to a solution of 4-hydroxymethyl-5-(2-phenylsulfonylethyl)thio-1,3-thiazole (1.69 g, 5.36 mmol) in N,N-dimethylformamide (5 mL). After 2 h, the mixture was partitioned between ethyl acetate and water. The organic solution was washed with 5% aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated to dryness, affording 1.78 g of the title compound. 1H NMR (CDCl3) δ3.05 (2H), 3.35 (2H), 4.70 (2H), 7.50-7.85 (5H), 8.82 (s, 1H).

Workup

  1. waitAfter 2 h
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic solution was washed with 5% aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f2d32020292a4ffc8a94e77beb973dce
Source dataset
uspto-grants-2000_02
Patent number
US06030965

Reaction notes

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