تفاعل #1120080

معادلة التفاعل

Cyclohexylmethyl bromide

1,2,4-triazole-3-thiol

sodium methoxide

→

cyclohexylmethyl 1,2,4-triazol-3-yl sulfide

المردود 81.1%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed for 4 h
2. 2
   أخرىevaporated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (400 ml)
4. 4
   أخرىThe organic phase is separated
5. 5
   غسيلwashed with water (100 ml)
6. 6
   تجفيفdried (Na2SO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىits volume reduced by evaporation
9. 9
   أخرىto precipitate
10. 10
    ترشيحThe solid was filtered off
11. 11
    أخرىdried

الإجراء التجريبي

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).

المصدر