Hydrochloric Acid → HCID 178470333, compound

HRID 1728953Notes

Reaction equation

HRID 1728953 reaction equation
[Na].[C:2](OCC)(=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:12]([O:14][C:15](=[O:26])[CH2:16][N:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C=O)[CH3:13].[Cl-].[Na+].[S-:29][C:30]#[N:31].[K+].Cl>CCOCC.C(O)C.O>[SH:29][C:30]1[N:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:16]([C:15]([O:14][CH2:12][CH3:13])=[O:26])=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:31]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7268Diethyl OxalateHCID 516872Potassium thiocyanateHCID 5360545SodiumHCID 14416604ethyl 2-(N-phenylformamido)acetate

Product 1

HCID 178470333HCID 178470333, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Absolute ethanol (50 mL) was slowly added to a mechanically stirred suspension of finely cut sodium metal (19.3 g; 0.84 mol) in anhydrous ether (500 mL). When most of the metal had dissolved, diethyl oxalate (114 mL; 0.84 mol) was slowly added followed by the slow addition of the N-phenyl-N-formylglycine ethyl ester (130 g; 0.67 mol). The mixture was stirred at room temperature overnight and then ice-water (700 mL) was added. The resulting emulsion was broken by sequential addition of a saturated sodium chloride solution (150 mL) and water (200 mL). The aqueous layer was removed, potassium thiocyanate (114 g; 1.18 mol) was added, then concentrated hydrochloric acid (160 mL), followed by absolute ethanol (900 mL). The resultant mixture was warmed at 60°-65° C. for 1 hour, then at 50° C. for 6 hours and finally allowed to stir at room temperature overnight. The light yellow precipitate was filtered, washed with ethanol and dried to give 103 g (48%) of diethyl 2-mercapto-1-phenyl-4,5-imidazoledicarboxylate (mp 145°-146° C.).

Workup

  1. dissolutionWhen most of the metal had dissolved
  2. customThe aqueous layer was removed
  3. waitat 50° C. for 6 hours
  4. stirringto stir at room temperature overnight
  5. filtrationThe light yellow precipitate was filtered
  6. washwashed with ethanol
  7. customdried

Sources & evidence

ORD record
ord-1706884c5fd742b48f17201e467f3009
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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