Dichloromethane → 5-(2-Acetamidomethyl-propan-2-yl)-2-(4-methylphenyl)benzimidazole

HRID 1639139Notes

Reaction equation

HRID 1639139 reaction equation
[C:1]([NH:4][CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([NH2:16])[CH:10]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2].ClCCl.[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][CH:22]=1>C(N(CC)CC)C>[C:1]([NH:4][CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]2[N:15]=[C:20]([C:21]3[CH:29]=[CH:28][C:24]([CH3:25])=[CH:23][CH:22]=3)[NH:16][C:11]=2[CH:10]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 134054-Methylbenzoyl ChlorideHCID 141530264-(2-Acetamidomethylprop-2-yl)-1,2-diaminobenzene

Product 1

HCID 198404055-(2-Acetamidomethyl-propan-2-yl)-2-(4-methylphenyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 4.4 g. of the 4-(2-acetamidomethylpropan-2-yl)-1,2-diaminobenzene (prepared in Example 1f) in 120 ml. dry dichloromethane are added 3.3 ml. triethylamine and then, with ice cooling, 3.06 g. 4-methylbenzoic acid chloride. After stirring the reaction mixture for 3 hours at ambient temperature, the solvent is removed in a vacuum. The residue is dissolved in water and extracted three times with dichloromethane, the organic phase is dried over anhydrous sodium sulphate, filtered and the solvent is removed in a vacuum. The residue (6.7 g.) is dissolved in glacial acetic acid and stirred for 3 hours at 70° C. The solvent is removed in a vacuum and the residue is purified by column chromatography (silica gel; dichloromethane containing 5% methanol). There is obtained 1.55 g. of the title compound; m.p. 230°-232° C.

Workup

  1. customthe solvent is removed in a vacuum
  2. dissolutionThe residue is dissolved in water
  3. extractionextracted three times with dichloromethane
  4. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed in a vacuum
  7. dissolutionThe residue (6.7 g.) is dissolved in glacial acetic acid
  8. stirringstirred for 3 hours at 70° C
  9. customThe solvent is removed in a vacuum
  10. customthe residue is purified by column chromatography (silica gel; dichloromethane containing 5% methanol)
  11. customThere is obtained 1.55 g

Sources & evidence

ORD record
ord-6fe75e5d46cb498da1975a820bb4090b
Source dataset
uspto-grants-1989_11
Patent number
US04882342

Reaction notes

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