Dichloromethane → HCID 54192258, compound

HRID 1639142Notes

Reaction equation

HRID 1639142 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[C:14]2[NH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH3:4].ClCCl.[C:26](Cl)(=[O:30])[CH:27]([CH3:29])[CH3:28]>C(N(CC)CC)C>[CH:27]([C:26]([NH:1][CH2:2][C:3]([C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[NH:11][C:10]=2[CH:14]=1)([CH3:4])[CH3:5])=[O:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 62325Isobutyryl chlorideHCID 178488841HCID 178488841, compound

Product 1

HCID 54192258HCID 54192258, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.9 g. 4-(2-Aminomethylpropan-2-yl)-2-(4-methoxyphenyl)-benzimidazole (obtained in Example 6) in 200 ml. dichloromethane are reacted with 2.5 ml. triethylamine and 0.82 g. isobutyric acid chloride at ambient temperature. After 10 hours, the solvent is removed in a vacuum and the residue is digested with water and 2N aqueous ammonia solution. The reaction mixture is extracted 4 times with dichloromethane and the organic phase is dried over anhydrous sodium sulphate, filtered and evaporated. Ethyl acetate is added thereto, a part thereof is distilled off with the dichloromethane and left to crystallise and the product is filtered with suction. The product is recrystallised from ethyl acetate to give 0.6 g. of the title compound; m.p. 218°-220° C.

Workup

  1. customat ambient temperature
  2. customthe solvent is removed in a vacuum
  3. extractionThe reaction mixture is extracted 4 times with dichloromethane
  4. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. additionEthyl acetate is added
  8. distillationa part thereof is distilled off with the dichloromethane
  9. waitleft
  10. customto crystallise
  11. filtrationthe product is filtered with suction
  12. customThe product is recrystallised from ethyl acetate
  13. customto give 0.6 g

Sources & evidence

ORD record
ord-40bc2e5cef4a4e9e8b5f98d74ea9998f
Source dataset
uspto-grants-1989_11
Patent number
US04882342

Reaction notes

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