Hydrochloric Acid → HCID 19026921, compound

HRID 1032905Notes

Reaction equation

HRID 1032905 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[NH:9]1[CH:13]=[N:12][C:11]([S:14]([CH2:17][CH:18]2[CH2:21][CH2:20][CH2:19]2)(=[O:16])=[O:15])=[N:10]1.Cl>N1C=CC=CC=1>[CH:18]1([CH2:17][S:14]([C:11]2[N:12]=[CH:13][N:9]([C:4]([N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[O:5])[N:10]=2)(=[O:16])=[O:15])[CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6916Diethylcarbamoyl chlorideHCID 178527386HCID 178527386, compound

Product 1

HCID 19026921HCID 19026921, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Diethylcarbamoyl chloride (1.49 ml; 11.3 mmol) was added to cyclobutylmethyl 1,2,4-triazol-3-yl sulfone (2.06 g; 10.2 mmol) in dry pyridine (10 ml) under dry nitrogen, and the solution stirred at room temperature overnight. The reaction mixture was poured into cold 2M hydrochloric acid (60 ml) and the cloudy solution extracted with two portions of ethyl acetate (120 ml and 50 ml). The extracts were combined, washed with saturated brine (50 ml), dried (Na2SO4), filtered and the volume of solution reduced by evaporation until a white solid precipitates. Hexane was added to the mixture which was then cooled and the solid filtered off to afford 3-(cyclobutylmethylsulfonyl)-N,N-diethyl-1,2,4-triazole-1-carboxamide (2.40 g; 78%) as white crystals, m.p. 113°-116° C., (Found, C: 47.96; H: 6.56; N: 18.51; S: 10.85. C12H20N4O3S requires C: 47.98; H: 6.71; N: 18.65; S: 10.67%). NMR - d(CDCl3 ; 60 MHz) 1.3 (6H, t, J=7 Hz), 1.5-2.4 (6H, m), 2.4-3.2 (1H, m), 3.4-3.8 (6H, m) and 8.9 (1H, s). IR vmax (CHCl3) 3000, 1710, 1440, 1340, 1270, 1180, 1145, 1030 and 870 cm-1.

Workup

  1. extractionthe cloudy solution extracted with two portions of ethyl acetate (120 ml and 50 ml)
  2. washwashed with saturated brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe volume of solution reduced by evaporation until a white solid
  6. customprecipitates
  7. additionHexane was added to the mixture which
  8. temperaturewas then cooled
  9. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-b5955123909945b6be4e90d490694c29
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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