Hydrochloric Acid → HCID 13536373, compound

HRID 1032902Notes

Reaction equation

HRID 1032902 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[CH2:20][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:15])=[O:16])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6916Diethylcarbamoyl chlorideHCID 178527385HCID 178527385, compound

Product 1

HCID 13536373HCID 13536373, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Diethylcarbamoyl chloride (1.55 ml; 11.8 mmol) was added to cyclopropylmethyl 1,2,4-triazol-3-yl sulfone (2.07 g; 11.1 mmol) in dry pyridine (10 ml) under dry nitrogen. The resulting solution was stirred at room temperature overnight. The resulting mixture was poured into cold 2M hydrochloric acid (40 ml) and the cloudy solution extracted into ethyl acetate (3×50 ml). The extracts were combined, washed with saturated brine (50 ml), dried (Na2SO4), filtered and evaporated to afford 3-(cyclopropylmethylsulfonyl)-N,N-diethyl-1,2,4-triazole-1-carboxamide (3.10 g; 98%) as white crystals, m.p. 68°-74° C., (Found, C: 46.23; H: 6.24; N: 19.60; S: 11.29. C11H18N4O3S requires C: 46.14; H: 6.34; N: 19.57; S: 11.20%) NMR - d(CDC13; 60 MHz) 0.2-0.9 (4H, m), 0.9-1.5 (7H, m), 3.3 (2H, d, J= 7 Hz), 3.6 (4H, q, J=7 Hz) and 8.9 (1H, s). IR vmax (CHCl3) 3040, 1710, 1440, 1340, 1270, 1180, 1150, 1030, 870 and 635 cm-1.

Workup

  1. extractionthe cloudy solution extracted into ethyl acetate (3×50 ml)
  2. washwashed with saturated brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7fb9861988ef4a53b41a0f9a152cf12b
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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