Allyl bromide → 5-[4-(1,1-Dimethylethyl)phenyl]-4-(2-propenylthio)-1,2,3-thiadiazole

HRID 2073370Notes

Reaction equation

HRID 2073370 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][N:14]=[N:13][C:12]=2[SH:16])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[K].[CH2:18](Br)[CH:19]=[CH2:20]>C(O)C>[CH3:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:15][N:14]=[N:13][C:12]=2[S:16][CH2:20][CH:19]=[CH2:18])=[CH:9][CH:10]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 5462222PotassiumHCID 14294241HCID 14294241, compound

Product 1

HCID 217680705-[4-(1,1-Dimethylethyl)phenyl]-4-(2-propenylthio)-1,2,3-thiadiazoleYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.45 g of 5-[4-(1,1-dimethylethyl)phenyl]-1,2,3-thiadiazole-4-thiol, potassium salt in 50 ml of ethanol was stirred overnight with 3.0 g of allyl bromide. The solvent was removed in vacuo, the residue taken up in ether, filtered and concentrated in vacuo. The residual oil was dissolved in a small amount of dichloromethane and purified on thick layer silica gel plates, eluting with the same solvent. The active fraction gave 1.225 g of the desired compound as a yellow oil. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90MHz: 1.39 (s, 9H, t-butyl); 3.98 (bd, 2H, SCH2); 5.05 (bd, 1H, CH=); 5.20 (bd, 1H, =CH); 5.87 (m, 1H, CH2CH=); 7.55 (s, 4H, C6H4). Infrared absorption spectrum (neat): 1640(w); 1615(w); 1525(w); 1480(w); 1475(w); 1450(w); 1410(w); 1370(w); 1270(w); 930(s); 820(s).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residual oil was dissolved in a small amount of dichloromethane
  5. custompurified on thick layer silica gel plates
  6. washeluting with the same solvent

Sources & evidence

ORD record
ord-3996acd1fbbe471f9b5fa6fccdd4f1bc
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

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