Chloroacetyl chloride → N-(chloroacetyl)-3,3-dimethyl-7-nitrobenzisoselenazoline

HRID 366409Notes

Reaction equation

HRID 366409 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[Se:4][NH:3]1.C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25].[Cl-].C([NH+](CC)CC)C>C1COCC1.C(OCC)(=O)C.O>[Cl:22][CH2:23][C:24]([N:3]1[C:2]([CH3:14])([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[Se:4]1)=[O:25]

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 98815673,3-Dimethyl-7-nitrobenzisoselenazolineHCID 12698378Triethylazanium chloride

Product 1

HCID 22448500N-(chloroacetyl)-3,3-dimethyl-7-nitrobenzisoselenazoline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3,3-dimethyl-7-nitrobenzisoselenazoline (1.28 g, 5 mmol), in 20 ml of anhydrous THF, containing triethylamine (0.83 ml, 6 mmol), cooled to 5° C. by an ice bath, is added dropwise chloroacetyl chloride (0.48 ml, 6 mmol). The dark brown reaction medium lightens rapidly, becoming luminous orange; as soon as the addition of the acid chloride is complete, a considerable precipitate, corresponding to triethylammonium chloride, appears. The amide formation reaction is exothermic. The ice bath is taken away and stirring is continued for about 1 hour at room temperature. After the addition of 20 ml of water and 20 ml of ethyl acetate, followed by separation, the organic phase is washed with 10 ml of a saturated aqueous solution of NaCl, then dried over MgSO4 and evaporated.

Workup

  1. customfollowed by separation
  2. washthe organic phase is washed with 10 ml of a saturated aqueous solution of NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-dc62d31d46184a17ac43e855aefd4804
Source dataset
uspto-grants-2000_10
Patent number
US06130212

Reaction notes

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