Diphosgene → HCID 57671585, compound

HRID 553533Notes

Reaction equation

HRID 553533 reaction equation
[I:1][C:2]1[CH:14]=[N:13][C:5]2[N:6]([CH3:12])[C:7](=[O:11])O[C:9](=[O:10])[C:4]=2[CH:3]=1.IC1C=NC(NC)=[C:20](C=1)[C:21]([O:23][CH3:24])=[O:22].IC1C=NC(NC)=C(C=1)C(OCC)=O.ClC(OC(Cl)(Cl)Cl)=O>ClCCCl.O1CCOCC1>[OH:10][C:9]1[C:4]2[C:5](=[N:13][CH:14]=[C:2]([I:1])[CH:3]=2)[N:6]([CH3:12])[C:7](=[O:11])[C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 4

HCID 10426DiphosgeneHCID 57671587HCID 57671587, compoundHCID 57671598HCID 57671598, compoundHCID 57671677HCID 57671677, compound

Product 1

HCID 57671585HCID 57671585, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

6-Iodo-1-methyl-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione. To a mixture of methyl 5-iodo-2-(methylamino)nicotinate and ethyl 5-iodo-2-(methylamino)nicotinate (10.5 g) and 1,4-dioxane (10 mL) in anhydrous 1,2-dichloroethane (1000 mL) was added trichloromethyl chloroformate (15.43 mL, 128.45 mmol) dropwise over 1 hour, with stirring and heating at 80° C. After addition, the reaction mixture was stirred at 80° C. for 4 hours, and was allowed to reach room temperature. The solvent was evaporated, and the residue was washed with a 1:1 mixture of EtOAc/hexanes (100 mL) and dried in vacuo to give the title compound.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at 80° C. for 4 hours
  3. customto reach room temperature
  4. customThe solvent was evaporated
  5. washthe residue was washed with a 1:1 mixture of EtOAc/hexanes (100 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e678edbac1564756aed45dfcb71fffad
Source dataset
uspto-grants-2011_11
Patent number
US08048894B2

Reaction notes

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