2-(Chloromethyl)-5,6-dimethylaniline hydrochloride → HCID 178423502, compound

HRID 1071549Notes

Reaction equation

HRID 1071549 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH2:14][C:15]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[C:16]=1[NH2:17]>C(O)(C)C>[CH3:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][CH2:14][C:15]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[C:16]=3[NH2:17])=[N:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 223940772-(Chloromethyl)-5,6-dimethylaniline hydrochlorideHCID 178423448HCID 178423448, compound

Product 1

HCID 178423502HCID 178423502, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 1 using 207 mg of 2-mercapto-5-methylbenzimidazole instead of 2-mercaptobenzimidazole and 260 mg of 2-(chloromethyl)-5,6-dimethylaniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline in isopropyl alcohol. The basic extraction used 10% sodium hydroxide instead of sodium carbonate. The dichloromethane extract was dried over sodium sulfate, filtered, and concentrated in vacuo to 274 mg of the title compound as a gum. The compound was used in subsequent reactions without further purification.

Workup

  1. extractionThe basic extraction
  2. extractionThe dichloromethane extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to 274 mg of the title compound as a gum
  6. customThe compound was used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-6de8f0a9b4c8403eb93198d40ed4d32e
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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