(4-Chlorophenyl)acetic acid → 2-(4-Chlorobenzyl)-4-methoxy-7-methylbenzimidazole

HRID 1650668Notes

Reaction equation

HRID 1650668 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH3:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=O)=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[NH:8][C:7]3[C:6]([O:9][CH3:10])=[CH:5][CH:4]=[C:3]([CH3:11])[C:2]=3[N:1]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 139713463-Methoxy-6-methylbenzene-1,2-diamine

Product 1

HCID 139713472-(4-Chlorobenzyl)-4-methoxy-7-methylbenzimidazoleYield 40.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2,3-diamino-4-methoxytoluene [prepared by hydrogenation of 4-methoxy-2,3-dinitrotoluene (7.5 g) over 10% palladium-carbon (2.5 g) in ethanol] and 4-chlorophenylacetic acid (23 g) was heated at 130°-150° C. for 4.5 h under nitrogen. The mixture was cooled, dissolved in chloroform, washed with 10% sodium carbonate solution, then with water, dried (Na2SO4) and evaporated to dryness in vacuo. The product was recrystallized from chloroform-pentane to afford the title compound, (5.75 g), m.p. 195°-197° C.

Workup

  1. temperaturewas heated at 130°-150° C. for 4.5 h under nitrogen
  2. temperatureThe mixture was cooled
  3. washwashed with 10% sodium carbonate solution
  4. dry with materialwith water, dried (Na2SO4)
  5. customevaporated to dryness in vacuo
  6. customThe product was recrystallized from chloroform-pentane

Sources & evidence

ORD record
ord-f5badeb539e5492e93dc7ea8b9e42265
Source dataset
uspto-grants-1990_05
Patent number
US04925853

Reaction notes

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