Semicarbazide hydrochloride → HCID 53960437, compound

HRID 436741Notes

Reaction equation

HRID 436741 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].[C:9]([N:13]=[N:14][C:15]1([N:21]=[C:22]=[S:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:12])([CH3:11])[CH3:10]>CO>[C:9]([N:13]=[N:14][C:15]1([NH:21][C:22]([NH:2][NH:3][C:4]([NH2:6])=[O:5])=[S:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 14798Sodium HydroxideHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexane

Product 1

HCID 53960437HCID 53960437, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.49 grams (0.0223 moles) of semicarbazide hydrochloride in 25 ml of methanol in a 50 ml erlenmeyer flask was added 1.75 grams (0.0223 moles) of 50% NaOH and the reaction stirred 15 minutes. To this solution was added 5.15 grams (0.0223 moles) of 1-t-butylazo-1-isothiocyanatocyclohexane and the reaction mixture stirred for 6 days at room temperature. The methanol was evaporated under reduced pressure, the residue slurried in water and filtered. The filter cake weighed 5.0 grams (73% crude yield) after drying and was a pale yellow solid. The product did not melt but decomposed around 180° C. The infrared spectrum of the product contained amide carbonyls at 1620 and 1675 cm-1, a strong band at 1540 cm-1 [-N(H)CS], a strong NH band at 3200 cm-1 and weaker NH bands around 3400 cm-1. The isothiocyanate band at 2040 cm-1 was absent.

Workup

  1. stirringthe reaction mixture stirred for 6 days at room temperature
  2. customThe methanol was evaporated under reduced pressure
  3. filtrationfiltered
  4. customafter drying
  5. customdecomposed around 180° C

Sources & evidence

ORD record
ord-608d3c1f46aa4abda961b8c55341c749
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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