Hydrochloric Acid → 2-(3-aminophenyl)-4-(4-chlorobenzyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1799483Notes

Reaction equation

HRID 1799483 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10][N:9]([C:16]3[CH:17]=[C:18]([NH:22]C(=O)C)[CH:19]=[CH:20][CH:21]=3)[C:8]2=[O:26])=[CH:4][CH:3]=1.Cl>C1COCC1>[NH2:22][C:18]1[CH:17]=[C:16]([N:9]2[C:8](=[O:26])[N:7]([CH2:6][C:5]3[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59139822N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

Product 1

HCID 687024682-(3-aminophenyl)-4-(4-chlorobenzyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dioneYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 9 Step 1: A mixture of N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H) yl)phenyl)acetamide (500 mg, 1.24 mmol) in a solution 6N of HCl (10 mL) and THF (10 mL) was stirred at reflux for 3 hours. The THF was evaporated and the aqueous layer was basified with saturated solution of NaHCO3 until neutral pH. The aqueous layer was then extracted with ethyl acetate (×3). The organic layers were combined to be successively washed with water then with brine, dried over MgSO4, filtered and concentrated. The crude product was azeotroped with acetonitrile to afford 2-(3-aminophenyl)-4-(4-chlorobenzyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione as a beige solid (423 mg, 94.5%).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe THF was evaporated
  3. extractionThe aqueous layer was then extracted with ethyl acetate (×3)
  4. washto be successively washed with water
  5. dry with materialwith brine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was azeotroped with acetonitrile

Sources & evidence

ORD record
ord-f9fdb3d13cfa405db02d99e6fac630cf
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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