Hydrochloric Acid → HCID 178470336, compound

HRID 1728956Notes

Reaction equation

HRID 1728956 reaction equation
C(O)C.[Na].[C:5](OCC)(=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH2:15]([O:17][C:18](=[O:23])[CH2:19][NH:20]C=O)[CH3:16].[S-:24][C:25]#[N:26].[K+].Cl>CCOCC.O>[SH:24][C:25]1[NH:20][C:19]([C:18]([O:17][CH2:15][CH3:16])=[O:23])=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:26]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7268Diethyl OxalateHCID 76615Glycine, N-formyl-, ethyl esterHCID 516872Potassium thiocyanateHCID 5360545Sodium

Product 1

HCID 178470336HCID 178470336, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Absolute ethanol (58 g; 1.25 mol) was added to a suspension of clean sodium (29 g; 1.25 g atom cut into small pieces) in anhydrous ether (700 mL). Diethyl oxalate (182 g; 1.25 mol) was added slowly to this mixture so that the exothermic reaction did not become too vigorous. The N-formyl-glycine ethyl ester (131 g; 1.0 mol) was added dropwise with stirring to the resulting solution and a red-brown precipitate formed. The mixture was allowed to stand overnight then water (1 L) was added to dissolve the precipitate and the ether layer was separated. Potassium thiocyanate (170 g; 1.75 mol) and concentrated hydrochloric acid (240 mL) were added to the aqueous solution. The yellow aqueous solution was slowly heated to 40°-60° C. for 6 hours and cooled. The yellow granular precipitate was filtered. The filtrate was concentrated to give an additional amount of the same product. The total product yield of 109.0 g (45%) of diethyl 2-mercapto-4,5-imidazoledicarboxylate was obtained.

Workup

  1. customa red-brown precipitate formed
  2. dissolutionto dissolve the precipitate
  3. customthe ether layer was separated
  4. temperatureThe yellow aqueous solution was slowly heated to 40°-60° C. for 6 hours
  5. temperaturecooled
  6. filtrationThe yellow granular precipitate was filtered
  7. concentrationThe filtrate was concentrated
  8. customto give an additional amount of the same product

Sources & evidence

ORD record
ord-5d8c7bae09264dd9b2f552ca1213f423
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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