2-(Chloromethyl)aniline--hydrogen chloride (1/1) → 2-[[(4-Methyl-1H-benzimidazol-2-yl)thio]methyl]benzenamine

HRID 1586468Notes

Reaction equation

HRID 1586468 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH2:14][C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17]>>[CH3:11][C:10]1[C:4]2[N:3]=[C:2]([S:1][CH2:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[NH2:17])[NH:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178424004HCID 178424004, compound

Product 1

HCID 140646492-[[(4-Methyl-1H-benzimidazol-2-yl)thio]methyl]benzenamineYield 23.1%

Procedure

The title compound was prepared by the method of Example 1 using 3.52 g of 2-mercapto-4-methylbenzimidazole instead of 2-mercaptobenzimidazole and 3.52 g of 2-(chloromethyl) aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline. Recrystallization from diethyl ether gave 1.23 g of the title compound: m.p. 125-127° C. Anal. Calc'd. for C15H15N3S: C, 66.89; H, 5.61; N,15.60; S, 11.90. Found: C, 66.76; H, 5.62; N, 15.41; S, 11.87.

Workup

  1. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-39a7d41dfe6e4d3caf53106c56e6a9d1
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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