Water → HCID 15285939, compound

HRID 2289398Notes

Reaction equation

HRID 2289398 reaction equation
[CH3:1][C:2]1([CH3:11])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[Se:4][NH:3]1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20].O>C(OCC)C>[C:19]([N:3]1[C:2]([CH3:11])([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[Se:4]1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9990749HCID 9990749, compound

Product 1

HCID 15285939HCID 15285939, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The derivative 3,3-dimethyl-benzisoselenazoline (148 mg; 0.7 mmole) was dissolved at room temperature in ethyl ether (4 ml). Triethylamine (107 μl; 0.77 mmole) and acetyl chloride (54 μl; 0.77 mmole) were added. A white precipitate appeared immediately. After 1 h, 1 ml of water was added to the reaction mixture. The crude product was extracted with 3×20 ml of dichloroethane. The organic phases were combined, washed with 2×20 ml of a saturated NaCl solution, dried over MgSO4 then filtered. The solvent was evaporated off under reduced pressure. The desired product was obtained after purification by liquid chromatography on a silica column (eluent: cyclohexane-ethyl acetate, 1/1).

Workup

  1. extractionThe crude product was extracted with 3×20 ml of dichloroethane
  2. washwashed with 2×20 ml of a saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationthen filtered
  5. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-21f738b22e344ec3b473728ae83c4ad6
Source dataset
uspto-grants-2000_07
Patent number
US06093532

Reaction notes

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