Hydrochloric Acid → HCID 15575766, compound

HRID 1660322Notes

Reaction equation

HRID 1660322 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[S:15])[NH:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na].[C:17](OCC)(=[O:23])[C:18](OCC)=[O:19].Cl>CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:18](=[O:19])[C:17](=[O:23])[NH:14][NH:13][C:12]1=[S:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5360545SodiumHCID 13278825HCID 13278825, compound

Product 1

HCID 15575766HCID 15575766, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-(2-tert.-Butoxycarbonylamino-ethyl)-thiosemicarbazide (9.37 g) is added to a solution of sodium (0.92 g) in methanol (40 cc) at 20° C., and diethyl oxalate (5.4 g) is then introduced dropwise in the course of 10 minutes. The mixture is heated under reflux for 3 hours. It is allowed to cool, water (100 cc) is added, concentrated hydrochloric acid (3 cc) is introduced dropwise, the mixture is extracted with ethyl acetate (2×100 cc) and the extract is washed with a saturated sodium chloride solution (2×50 cc), dried ocer sodium sulphate, filtered and concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). The residue is taken up in methylene chloride (65 cc), the crystallisation is started, the batch is left for 2 hours at 20° C. and then filtered, and white crystals (4.59 g) of 4-(2-tert.-butoxycarbonylamino-ethyl)-5,6-dioxo-3-thioxoperhydro-1,2,4-triazine, melting at 160° C., are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. extractionthe mixture is extracted with ethyl acetate (2×100 cc)
  5. washthe extract is washed with a saturated sodium chloride solution (2×50 cc)
  6. dry with materialdried ocer sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  9. customthe crystallisation
  10. filtrationfiltered

Sources & evidence

ORD record
ord-fe515f2f653246859a352da497d480d7
Source dataset
uspto-grants-1981_12
Patent number
US04307116

Reaction notes

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