Diphosgene → HCID 86760970, compound

HRID 1822195Notes

Reaction equation

HRID 1822195 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][CH:7]=1.ClC(OC(Cl)(Cl)Cl)=[O:21]>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9]3[N:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11](=[O:12])[O:13][C:14]2=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10426Diphosgene2×HCID 23083419HCID 23083419, compound

Product 1

HCID 86760970HCID 86760970, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of methyl 2-(3-fluorophenylamino)-nicotinate (4.90 g, 16.2 mmol; synthesized according to WO, A, 01/42244) in 1,2-dichloroethane (80 ml ) was added at 80° C. trichloromethyl chloroformate (also called: diphosgene, 5.9 ml, 48.3 mmol) gradually dropwise over about 30 minutes. Three hours later, activated carbon (130 mg) was added, and the mixture was heated under reflux for 30 minutes, filtered off, and then evaporated. The resultant residue was washed with isopropyl ether, and dried to give 1-(3-fluorophenyl)-2H-pyrido[2,3-d][1,3]oxazin-2,4(1H)-dione(3.42g, 82%) as crystals.

Workup

  1. additionThree hours later, activated carbon (130 mg) was added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationfiltered off
  5. customevaporated
  6. washThe resultant residue was washed with isopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-92df26ef4472433a95920249b3cb5908
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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