N-Iodosuccinimide → HCID 18795525, compound

HRID 1003157Notes

Reaction equation

HRID 1003157 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[O:15][CH2:14][N:13]([C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12](=[O:24])[CH:11]=1>C(O)(=O)C>[I:1][C:11]1[C:12](=[O:24])[N:13]([C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][O:15][C:10]=1[CH3:9]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 18795541HCID 18795541, compound

Product 1

HCID 18795525HCID 18795525, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
42.5 °C

Procedure

N-Iodosuccinimide (238 g) was added to a stirred solution of ethyl 2-(2,3-dihydro-6-methyl-4-oxo-4H-1,3-oxazin-3-yl)-2-methylpropanoate (200 g) in acetic acid. The mixture was stirred at 40-45° C. for 5 hours then at ambient temperature overnight and evaporated. The residue was diluted with ether, washed with water, sodium carbonate solution (2M) and brine, dried (MgSO4) and evaporated. A solution of the residue in ethanol was cooled to -40° C. to give ethyl 2-(2,3-dihydro-5-iodo-6-methyl-4-oxo-4H-1,3-oxazin-3-yl)-2-methylpropanoate (66.9 g), m.p. 85-87° C.

Workup

  1. customat ambient temperature overnight and evaporated
  2. additionThe residue was diluted with ether
  3. washwashed with water, sodium carbonate solution (2M) and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. temperatureA solution of the residue in ethanol was cooled to -40° C.

Sources & evidence

ORD record
ord-7b295aee12a64fccb0c23c8865aeff02
Source dataset
uspto-grants-2000_04
Patent number
US06046135

Reaction notes

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