Triphosgene → HCID 117761083, compound

HRID 523230Notes

Reaction equation

HRID 523230 reaction equation
[NH2:1][C:2]1[C:18]([F:19])=[CH:17][C:16]([F:20])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[C:8]=1[CH3:14])=[O:5].Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Br:13][C:9]1[C:8]([CH3:14])=[C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[C:18]([F:19])[CH:17]=[C:16]([F:20])[CH:15]=3)[NH:1][C:22]2=[O:24])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 117761100HCID 117761100, compound

Product 1

HCID 117761083HCID 117761083, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-N-(3-bromo-2-methylphenyl)-3,5-difluorobenzamide (760 mg, 2.23 mmol) in THF (10 mL) was treated portionwise with triphosgene (722 mg, 2.43 mmol). The solution was stirred at room temperature for 60 min, then was treated dropwise with saturated aqueous NaHCO3 and stirred until no more gas evolution was observed. The organic phase was separated, washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (40 g), eluting with EtOAc-hexanes (gradient from 0-100%), to give 3-(3-bromo-2-methylphenyl)-6,8-difluoroquinazoline-2,4(1H,3H)-dione (820 mg), used without further purification. Mass spectrum m/z 367, 369 (M+H)+, 389, 391 (M+Na)+.

Workup

  1. stirringstirred until no more gas evolution
  2. customThe organic phase was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (40 g)
  7. washeluting with EtOAc-hexanes (gradient from 0-100%)

Sources & evidence

ORD record
ord-402f34d6c1264860a8bece8abe477bf6
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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