Phosphorus tribromide → HCID 68702628, compound

HRID 1799476Notes

Reaction equation

HRID 1799476 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([CH2:14]O)=[N:10][N:9]([C:16]3[CH:17]=[C:18]([NH:22][C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][CH:21]=3)[C:8]2=[O:26])=[CH:4][CH:3]=1.P(Br)(Br)[Br:30]>C(#N)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([CH2:14][Br:30])=[N:10][N:9]([C:16]3[CH:17]=[C:18]([NH:22][C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][CH:21]=3)[C:8]2=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 59139899HCID 59139899, compound

Product 1

HCID 68702628HCID 68702628, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

According to Scheme 7 Step 6: To a solution of N-(3-(4-(4-chlorobenzyl)-6-(hydroxymethyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (500 mg, 1.25 mmol) in acetonitrile (20 mL) under nitrogen atmosphere was added phosphorus tribromide (176 μL, 1.87 mmol) dropwise and the mixture was refluxed for 90 min. The reaction mixture was diluted with 200 mL a saturated solution of NaHCO3 (200 mL) and the aqueous layer was extracted twice with DCM (200 mL). The organic layers were combined to be dried over MgSO4, filtered and concentrated under reduced pressure to afford N-(3-(4-(4-chlorobenzyl)-6-(bromomethyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 13(A) (540 mg, 93%) as a yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 90 min
  2. extractionthe aqueous layer was extracted twice with DCM (200 mL)
  3. dry with materialto be dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ab6ef7379a24f0c901d8a69d5c52c42
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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