Allyl bromide → 2-Allylsulfanyl-5,6-dimethyl-1H-benzoimidazole

HRID 843227Notes

Reaction equation

HRID 843227 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[CH:7][C:5]=2[N:6]=1.[CH2:13](Br)[CH:14]=[CH2:15].[OH-].[Na+].C(OC(=O)C)C>CCCCCC>[CH2:15]([S:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([CH3:12])[C:9]([CH3:11])=[CH:10][C:4]=2[N:3]=1)[CH:14]=[CH2:13]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178422342HCID 178422342, compound

Product 1

HCID 31246422-Allylsulfanyl-5,6-dimethyl-1H-benzoimidazoleYield 93%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2-Allylthio-5,6-dimethylbenzimidazole (III) was prepared as described above for I from 2,67 g (0,015 mol) 2-mercapto-5,6-dimethyl-benzimidazole, 2,1 g (0,017 mol) allylbromide in the presence 0,7 g (0,017 mol) sodium hydroxide, yield 2,5 g (76%), m.p. 119-120° C. (from mixture ethylacetate with hexane). 1H NMR (CDCl3), δ: 2,33 (6H, s, 2CH3); 3,89 (2H, d, CH2S); 5,10 (HB, d, CHC═CHAHB); 5,25 (HA,d, CHC═CHACHB); 7,30 (2H, broad s, ArH); 10,11 (1H, broad s, NH).

Sources & evidence

ORD record
ord-58e7d6f73a294f8787948415c15327f5
Source dataset
uspto-grants-2002_04
Patent number
US06376666B1

Reaction notes

Loading…