Chloroform → 2-[3-(4-Methylpyperazino)propylthio]-5,6-dimethylbenzimidazole

HRID 843228Notes

Reaction equation

HRID 843228 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.Cl.Cl.[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24]Cl)[CH2:18][CH2:17]1.[OH-].[Na+].C(Cl)(Cl)Cl>CCCCCC>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][S:1][C:2]2[NH:6][C:5]3[CH:7]=[C:8]([CH3:12])[C:9]([CH3:11])=[CH:10][C:4]=3[N:3]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 30140681-(3-Chloropropyl)-4-methylpiperazine dihydrochlorideHCID 178422342HCID 178422342, compound

Product 1

HCID 1317231952-[3-(4-Methylpyperazino)propylthio]-5,6-dimethylbenzimidazoleYield 79%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2-[3-(4-Methylpyperazino)propylthio]-5,6-dimethylbenzimidazole (XVII) and its trihydrochloride were synthesized as described above. The reaction of 2,8 g (0,010 mol) 2-mercapto-5,6-dimethylbenzimidazole and 3,74 g (0,015 mol) 3-(4-methylpyperazino)propylchloride dihydrochloride in the presence 1,32 g (0,033 mol) sodium hydroxide gave in 79% yield (2,5 g) compound XVII, m.p. 116-118° C. (with decomp., from chloroform with hexane). 1H NMR (CDCl3), δ: 1,95 (2H, m, CH2CH2CH2); 2,31 (6H, s, 2CH3); 2,35 (3H, s, CH2N); 2,54 (10H, broad m, 8H of pyperazine, 2H, t, CH2S); 3,22 (2H, t, CH2N); 7,50 (2H, broad s, ArH). Trihydrochloride of XVII, yield 78%, m.p. 228-231° C. (with decomp., from ethanol).

Sources & evidence

ORD record
ord-923df2c429c547dd8ea9b994a68298d9
Source dataset
uspto-grants-2002_04
Patent number
US06376666B1

Reaction notes

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