Ethoxyacetic acid → HCID 20545515, compound

HRID 2285607Notes

Reaction equation

HRID 2285607 reaction equation
[CH2:1]([O:3][CH2:4][C:5](O)=O)[CH3:2].[CH2:8]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=1)[CH2:9][CH2:10][CH3:11]>C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][C:5]1[NH:19][C:14]2[CH:13]=[C:12]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:17]=[CH:16][C:15]=2[N:18]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12301Ethoxyacetic acidHCID 193134-Butyl-1,2-benzenediamine

Product 1

HCID 20545515HCID 20545515, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

20.8 g of ethoxyacetic acid are added to 23 g of crude 4-butyl-1,2-phenylene-diamine and the mixture is heated at 130° for 90 minutes. It is allowed to cool and is taken up in ethyl acetate, washed with sodium bicarbonate solution and then three times with water, dried over sodium sulphate and filtered and the filtrate is evaporated to dryness under reduced pressure. The residue is chromatographed on 600 g of silica gel using chloroform as the solvent. After a small initial fraction, 2-ethoxymethyl-5-butyl-benzimidazole is obtained in the main fraction.

Workup

  1. temperaturethe mixture is heated at 130° for 90 minutes
  2. temperatureto cool
  3. washwashed with sodium bicarbonate solution
  4. dry with materialthree times with water, dried over sodium sulphate
  5. filtrationfiltered
  6. customthe filtrate is evaporated to dryness under reduced pressure
  7. customThe residue is chromatographed on 600 g of silica gel

Sources & evidence

ORD record
ord-ad48d066967a4272a5ba0304435ec392
Source dataset
uspto-grants-1982_04
Patent number
US04323688

Reaction notes

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