2-(Chloromethyl)aniline--hydrogen chloride (1/1) → HCID 178488113, compound

HRID 1586471Notes

Reaction equation

HRID 1586471 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH2:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>C(O)(C)C>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][CH2:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[NH2:18])=[N:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178488032HCID 178488032, compound

Product 1

HCID 178488113HCID 178488113, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 1 using 1.68 g (9.33 mMol) of 2-mercapto-5-methoxybenzimidazole instead of 2-mercaptobenzimidazole and 1.99 g (11.2 mMol) of 2-(chloromethyl)aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline in 250 ml of isopropyl alcohol. The basic extraction used 5% sodium hydroxide instead of sodium carbonate. Chromatography on silica gel, followed by crystallization from diethylether, gave 520 mg of pure title compound: m.p. 140-142° C. Anal. Calc'd. for C15H15N3OS: C, 63.14; H, 5.30; N,14.73; S, 11.23. Found: C, 63.44; H, 5.42; N, 14.43; S, 11.07.

Workup

  1. extractionThe basic extraction
  2. customChromatography on silica gel, followed by crystallization from diethylether

Sources & evidence

ORD record
ord-86356c6eae19491ba06ec6719fe2c891
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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