Hydrochloric Acid → HCID 19026924, compound

HRID 1032899Notes

Reaction equation

HRID 1032899 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[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:16])=[O:15])=[N:10]1.Cl>N1C=CC=CC=1.ClCCl>[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][CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6916Diethylcarbamoyl chlorideHCID 178527389HCID 178527389, compound

Product 1

HCID 19026924HCID 19026924, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Diethylcarbamoyl chloride (1.2 ml; 9.4 mmol) was added to cyclohexylmethyl 1,2,4-triazol-3-yl sulfone (2.0 g; 8.7 mmol) in dry pyridine (10 ml) under dry nitrogen, and the solution stirred at room temperature overnight. The resulting mixture was poured into 2M hydrochloric acid (40 ml) at 2° C. and the cloudy solution extracted into ethyl acetate (3×60 ml). The extracts were combined, dried (Na2SO4), filtered and evaporated, to afford a colorless oil which was dissolved in 95% dichloromethane, 5% acetonitrile, and the solution filtered through silica. Evaporation afforded 3-(cyclohexylmethylsulfonyl)-N,N-diethyl-1,2,4-triazole-1-carboxamide (2.82 g; 98%) as white crystals, m.p. 40°-46° C. (Found, C: 51.04; H: 7.39; N: 17.01; S: 9.81. C14H24N4O3S requires C: 51.20; H: 7.37; N: 17.06; S: 9.76%). NMR - d(CDCl3 ; 90 MHz) 0.80-2.30 (17H, m), 3.31 (2H, d, J=6.1 Hz), 3.61 (4H, m) and 8.92 (1H, s).

Workup

  1. extractionthe cloudy solution extracted into ethyl acetate (3×60 ml)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a colorless oil which
  6. filtration5% acetonitrile, and the solution filtered through silica
  7. customEvaporation

Sources & evidence

ORD record
ord-d2ed68abf89e4ca0bb0e96e2457ff1c4
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

Loading…