Hydrochloric Acid → HCID 19026936, compound

HRID 1032897Notes

Reaction equation

HRID 1032897 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[CH2:22][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][CH2:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6916Diethylcarbamoyl chlorideHCID 178527387HCID 178527387, compound

Product 1

HCID 19026936HCID 19026936, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Diethylcarbamoyl chloride (0.65 ml; 5.08 mmol) was added to cyclopentylmethyl 1,2,4-triazol-3-yl sulfone (1.00 g; 4.65 mmol) in dry pyridine (5 ml) under dry nitrogen, and the solution stirred at room temperature overnight. The resulting mixture was poured into 2M hydrochloric acid (20 ml) at 3° C. and the mixture extracted into ethyl acetate (3×30 ml). The extracts were combined, dried (Na2SO4), filtered and evaporated, to afford 3-(cyclopentylmethylsulfonyl)-N,N-diethyl-1,2,4-triazole-1-carboxamide (1.44 g; 99%) as white crystals, m.p. 77°-79° C., (Found, C: 49.82; H: 6.75; N: 17.96; S: 10.44. C13H22N4O3S requires C: 49.66; H: 7.05; N: 17.82; S: 10.20%) NMR - d(CDCl3 ; 60 MHz) 1.0-2.6 (15H, m), 3.3-3.8 (6H, m) and 9.0 (1H, s).

Workup

  1. extractionthe mixture extracted into ethyl acetate (3×30 ml)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-36bed1a8bdc24be38e184276c94a8fd7
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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