2-(Chloromethyl)-4-methylaniline hydrochloride → HCID 178466045, compound

HRID 1586484Notes

Reaction equation

HRID 1586484 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH2:16][C:17]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:18]=1[NH2:19]>C(O)(C)C>[CH2:12]([O:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][CH2:16][C:17]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:18]=3[NH2:19])=[N:3][C:4]=2[CH:10]=1)[CH3:13]

Participants

4

Reactant 2

HCID 223941892-(Chloromethyl)-4-methylaniline hydrochlorideHCID 178466039HCID 178466039, compound

Product 1

HCID 178466045HCID 178466045, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 1 using 3.00 g of 2-mercapto-5-ethoxybenzimidazole instead of 2-mercaptobenzimidazole and 3.71 g of 2-(chloromethyl)-4-methylaniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline in isopropyl alcohol. The basic extraction used 10% sodium hydroxide instead of sodium carbonate. Crystallization during concentration of the dichloromethane extract gave 2.13 g of the title compound, which was used in subsequent reactions without further purification.

Workup

  1. extractionThe basic extraction
  2. customCrystallization during concentration of the dichloromethane
  3. extractionextract

Sources & evidence

ORD record
ord-05cd634cea1f49a594c7953a017a8a82
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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