2-(Chloromethyl)aniline--hydrogen chloride (1/1) → HCID 178507504, compound

HRID 1071546Notes

Reaction equation

HRID 1071546 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl: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]>>[Cl: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

3

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178527787HCID 178527787, compound

Product 1

HCID 178507504HCID 178507504, compoundYield 63%

Procedure

The title compound was prepared by the method of Example 1 using 2.50 g of 2-mercapto-5-chlorobenzimidazole instead of 2-mercaptobenzimidazole and 2.42 g of 2-(chloromethyl)aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline. The basic extraction used 5% sodium hydroxide instead of sodium carbonate. Washing the solid residue from the dichloromethane extract with additional dichloromethane gave 2.47 g of the title compound. Analysis. Calc'd. for C14H12N3ClS: C, 58.03; H, 4.17; N, 14.10; S, 11.06; C1, 12.23. Found: C, 57.33; H, 4.06; N, 14.27; S, 10.99; C1, 12.74.

Workup

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

Sources & evidence

ORD record
ord-3878c92bc1c14d82a6236652085de1de
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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