Cyclohexane, (bromomethyl)- → HCID 178420906, compound

HRID 1032898Notes

Reaction equation

HRID 1032898 reaction equation
[CH:1]1([CH2:7]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:9]1[CH:13]=[N:12][C:11]([SH:14])=[N:10]1.C[O-].[Na+]>CO>[NH:9]1[CH:13]=[N:12][C:11]([S:14][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:10]1

Participants

5

Reactant 3

HCID 137636Cyclohexane, (bromomethyl)-HCID 10942334Sodium MethoxideHCID 178527894HCID 178527894, compound

Product 1

HCID 178420906HCID 178420906, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclohexylmethyl bromide (42 ml; 0.30 mol) was added over 5 min to 1,2,4-triazole-3-thiol (30.3 g; 0.30 mol) and sodium methoxide (17.3 g; 0.32 mol) in dry methanol (250 ml) under dry nitrogen. The mixture was refluxed for 4 h, stirred at room temperature overnight and evaporated. The residue was dissolved in ethyl acetate (400 ml) and water (200 ml). The organic phase is separated, washed with water (100 ml), dried (Na2SO4), filtered and its volume reduced by evaporation, causing a solid to precipitate. The solid was filtered off and dried, to afford cyclohexylmethyl 1,2,4-triazol-3-yl sulfide (48.0 g; 81%) as white plates, m.p. 74°-78° C. (Found, C: 54.98; H: 7.85; N: 21.32; S: 16.13. C9H15N3S requires C: 54.79; H: 7.66; N: 21.30; S: 16.25%). NMR - d(CDCl3 ; 90 MHz) 0.50-2.10 (11H, m), 3.1 (2H, d, J=6.4 Hz), 8.13 (1H, s) and 13.9 (1H, br s).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (400 ml)
  4. customThe organic phase is separated
  5. washwashed with water (100 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customits volume reduced by evaporation
  9. customto precipitate
  10. filtrationThe solid was filtered off
  11. customdried

Sources & evidence

ORD record
ord-eafdb23d2bc64b2aad2b7459a3386ca1
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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