Hydrochloric Acid → Ethyl 4-[2-(aminocarbothioyl)hydrazino]-4-oxobutanoate

HRID 1295265Notes

Reaction equation

HRID 1295265 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7](O)=[O:8])[CH3:2].C(OCCCl)=O.[NH2:17][NH:18][C:19]([NH2:21])=[S:20].Cl>O1CCCC1.O.C(N(CC)CC)C>[NH2:21][C:19]([NH:18][NH:17][C:7](=[O:8])[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:10])=[S:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 70610Monoethyl succinateHCID 2467482-Chloroethyl formateHCID 2723789Thiosemicarbazide

Product 1

HCID 22930781Ethyl 4-[2-(aminocarbothioyl)hydrazino]-4-oxobutanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of succinic acid monoethyl ester (22.0 g) and triethylamine (16.8 g) in tetrahydrofuran (150 ml) was added dropwise chloroethyl formate (18.0 g) at −20° C. After stirring for 30 min., pulverized thiosemicarbazide (13.7 g) was added and the mixture was stirred at room temperature for 7 hrs. Water was added to the reaction mixture, acidified with 2N hydrochloric acid and extracted with chloroform. The aqueous layer was separated and sodium chloride was added. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residual crystals were recrystallized from dichloromethane-ethanol to give ethyl 4-[2-(aminocarbothioyl)hydrazino]-4-oxobutanoate as colorless prism crystals (8.23 g, 25%). melting point: 143–144° C.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 7 hrs
  3. extractionextracted with chloroform
  4. customThe aqueous layer was separated
  5. additionsodium chloride was added
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residual crystals were recrystallized from dichloromethane-ethanol

Sources & evidence

ORD record
ord-b473733af0944ed5aa429a4bc0f0f3c7
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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