2-(Chloromethyl)aniline--hydrogen chloride (1/1) → HCID 178466044, compound

HRID 1586482Notes

Reaction equation

HRID 1586482 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]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>C(O)(C)C>[OH2:11].[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]=[CH:22][CH:21]=[CH:20][C:18]=3[NH2:19])=[N:3][C:4]=2[CH:10]=1)[CH3:13]

Participants

4

Reactant 2

HCID 123879412-(Chloromethyl)aniline--hydrogen chloride (1/1)HCID 178466039HCID 178466039, compound

Product 1

HCID 178466044HCID 178466044, compoundYield 106.1%

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 2.76 g of 2-(chloromethyl)aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline in 250 ml of isopropyl alcohol. The basic extraction used 5% sodium hydroxide instead of sodium carbonate. Crystallization during concentration of the dichloromethane extract gave 2.60 g of the title compound as the monohydrate: m.p. 87-89° C. Anal. Calc'd. for C16H17N3OS*H2O: C, 63.76; H, 5.68; N, 13.94; S, 10.64. Found: C, 63,65; H, 5.74; N, 13.89; S, 10.89.

Workup

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

Sources & evidence

ORD record
ord-a8f9443dcea74346b91cc214c7e892db
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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