2-(Chloromethyl)aniline--hydrogen chloride (1/1) → HCID 178507503, compound

HRID 1586483Notes

Reaction equation

HRID 1586483 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH2:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>C(O)(C)C>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][CH2:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[NH2:20])=[N:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178506086HCID 178506086, compound

Product 1

HCID 178507503HCID 178507503, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 1 using 4.36 g of 2-mercapto-5-(trifluoromethyl)benzimidazole instead of 2-mercaptobenzimidazole and 3.56 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 2.40 g of the title compound: m.p. ca. 155° C. Anal. Calc'd. for C15H12N3F3S: C, 55.72; H, 3.74; N, 13.00; S, 9.92; F, 17.63. Found: C, 55.55; H, 3.68; N, 13.10; S, 10.12; F, 17.38.

Workup

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

Sources & evidence

ORD record
ord-7586b82f64a54b819c4a2a34d6ba6854
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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