Hydrochloric Acid → HCID 22312924, compound

HRID 965640Notes

Reaction equation

HRID 965640 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:19](=[O:20])[NH:18][C:17](=[O:21])[CH:16]=[N:15]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[BH4-].[Na+].Cl>O.C(O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]([OH:7])[C:8]2[CH:9]=[CH:10][C:11]([N:14]3[C:19](=[O:20])[NH:18][C:17](=[O:21])[CH:16]=[N:15]3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 12846566HCID 12846566, compound

Product 1

HCID 22312924HCID 22312924, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

A mixture of 2-[4-(4-chlorobenzoyl)phenyl]-1,2,4-triazine-3,5-(2H,4H)-dione (0.05 mol), ethanol (150 ml), water (150 ml) and NaOH (50%; 10 ml) was stirred at 10° C. A mixture of NaBH4 (0.05 mol), water (50 ml) and NaOH (50%; 2 ml) was added dropwise during 15 minutes. After stirring for 3 hours, 300 ml ice was added. The mixture was acidified with concentrated HCl. The product was extracted with CHCl3, yielding 5.8 g of 2-[4-[(4-chlorophenyl)hydroxymethyl]phenyl]-1,2,4-triazine-3,5-(2H,4H)-dione (interm. 31). The organic layer was dried, filtered and evaporated. The residue was crystallized with 2-propanol. The product was filtered off, washed with 2,2′-oxybispropane and dried, yielding a second fraction of 5.5 g of intermediate 31.

Workup

  1. additionwas added dropwise during 15 minutes
  2. stirringAfter stirring for 3 hours
  3. extractionThe product was extracted with CHCl3

Sources & evidence

ORD record
ord-9f2889bd8d3447b3ad96196df64d7bc8
Source dataset
uspto-grants-2005_10
Patent number
US06951857B2

Reaction notes

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