2-(Chloromethyl)aniline--hydrogen chloride (1/1) → 2-[[(5,6-Dimethyl-1H-benzimidazol-2-yl)thio]methyl]benzenamine

HRID 1586470Notes

Reaction equation

HRID 1586470 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.Cl.Cl[CH2:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>>[CH3:12][C:11]1[C:2]([CH3:1])=[CH:3][C:4]2[NH:8][C:7]([S:9][CH2:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[NH2:18])=[N:6][C:5]=2[CH:10]=1

Participants

3

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178422342HCID 178422342, compound

Product 1

HCID 137541362-[[(5,6-Dimethyl-1H-benzimidazol-2-yl)thio]methyl]benzenamine

Procedure

The title compound was prepared by the method of Example 1 using 2.56 g of 5,6-dimethyl-2-mercaptobenzimidazole instead of 2-mercaptobenzimidazole and 2.56 g of 2-(chloromethyl) aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline. Instead of using sodium carbonate in an extraction, the crude precipitate was neutralized with triethylamine in methanol. Trituration of the resultant crude title compound with methanol and diethyl ether gave 2.0 g of analytically pure title compound. Anal. Calc'd. for C15H15N3S: C, 67.81; H, 6.05; N,14.83; S, 11.31. Found: C, 67.21; H, 6.16; N, 14.50; S, 11.06.

Workup

  1. extractionInstead of using sodium carbonate in an extraction

Sources & evidence

ORD record
ord-6fa6d112237b4e61b0049c76e3918f60
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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