Sodium Carbonate → HCID 10423103, compound

HRID 649001Notes

Reaction equation

HRID 649001 reaction equation
N[C:2]1[CH:3]=[C:4]([C:14]2[CH2:18][NH:17][C:16](=[O:19])[C:15]=2[CH2:20][CH3:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH3:13].[PH2](O)=O.N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>Cl.[Cu-]=O>[CH2:20]([C:15]1[C:16](=[O:19])[NH:17][CH2:18][C:14]=1[C:4]1[CH:3]=[CH:2][C:7]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])=[CH:6][CH:5]=1)[CH3:21]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 4124402Phosphinic AcidHCID 10333978HCID 10333978, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 10423103HCID 10423103, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 313Hydrochloric AcidSolvent

Procedure

4-[3-Amino-4-(2-methyl-1H-imidazol-1-yl)phenyl]-3-ethyl-1,5-dihydro-2H-pyrrol-2-one (2.0 g, 7.1 mmol) is dissolved in concentrated HCl (40 mL) at 5° C, and hypophosphorous acid (50% aqueous solution, 14.6 mL, 0.14 mol) is added dropwise. Aqueous sodium nitrite (2 N, 4.4 mL, 8.8 mmol) is added, and the mixture is stirred for 5 minutes. A trace amount of copper (I) oxide is added, and the mixture is stirred an additional 1 hr at 5° C. The mixture is neutralized with sodium carbonate, extracted with n-butanol, and the extracts are evaporated. The residue is triturated with methanol, filtered, and the filtrates are evaporated. Chromatography of the residue on silica gel followed by recrystallization from ethanol and drying under vacuum at 70° C. for 18 hr provides the title compound.

Workup

  1. stirringthe mixture is stirred an additional 1 hr at 5° C
  2. extractionextracted with n-butanol
  3. customthe extracts are evaporated
  4. customThe residue is triturated with methanol
  5. filtrationfiltered
  6. customthe filtrates are evaporated
  7. customChromatography of the residue on silica gel followed by recrystallization from ethanol
  8. customdrying under vacuum at 70° C. for 18 hr

Sources & evidence

ORD record
ord-824014beadb74544aa6e7338549b39a7
Source dataset
uspto-grants-1988_04
Patent number
US04737511

Reaction notes

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