2-(Chloromethyl)aniline--hydrogen chloride (1/1) → HCID 178423501, compound

HRID 1071545Notes

Reaction equation

HRID 1071545 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][CH:19]=[CH:18][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][CH:19]=[CH:18][C:16]=3[NH2:17])=[N:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178423448HCID 178423448, compound

Product 1

HCID 178423501HCID 178423501, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 1 using 2.50 g of 2-mercapto-5-methylbenzimidazole instead of 2-mercaptobenzimidazole and 2.71 g of 2-(chloromethyl)aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline in isopropyl alcohol. The basic extraction used 5% sodium hydroxide instead of sodium carbonate. Washing the solid residue from the dichloromethane extract with additional dichloromethane gave 1.65 g of the title compound. Analysis. Calc'd. for C15H15N3S: C, 66.89; H, 5.61; N, 15.60; S, 11.90. Found: C, 65.78; H, 5.48; N, 15.54; S, 11.94.

Workup

  1. extractionThe basic extraction
  2. washWashing the solid residue from the dichloromethane
  3. extractionextract with additional dichloromethane

Sources & evidence

ORD record
ord-4daeaabc322544a5ae4239bcf538ecc1
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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