Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 19864530, compound

HRID 1200000Notes

Reaction equation

HRID 1200000 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13].Cl.[C:15](=N)(OCC)[CH3:16]>C(O)C>[CH3:15][C:16]1[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:13]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 22184611HCID 22184611, compound

Product 1

HCID 19864530HCID 19864530, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-Hydroxybutylamino)phenylamine (3.6 g) and ethyl acetimidate hydrochloride (3.7 g) was dissolved in ethanol (20 ml) and stirred at room temperature for 11/2 hours. The mixture was evaporated under vacuum and the residue partitioned between ethyl acetate (30 ml) and water (20 ml). The organic phase was separated, dried over Na2SO4, filtered and evaporated to give the title compound as a brown oil (2.8 g).

Workup

  1. customThe mixture was evaporated under vacuum
  2. customthe residue partitioned between ethyl acetate (30 ml) and water (20 ml)
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0c718a80e73547efbc9cc9b3a0a51cde
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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