Hydrazine hydrate (1:1) → HCID 18794796, compound

HRID 400125Notes

Reaction equation

HRID 400125 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:26][CH2:27][CH3:28])C(N)=O)=[CH:17][CH:16]=1)[CH3:11].O.[NH2:30][NH2:31].CO[CH:34](OC)[N:35]([CH3:37])C>C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][O:26][CH2:27][CH2:28][C:34]2[NH:31][N:30]=[CH:37][N:35]=2)=[CH:17][CH:16]=1)[CH3:11]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 18794821HCID 18794821, compound

Product 1

HCID 18794796HCID 18794796, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

3-[4-[2-[N-(2-Benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-ethoxypropanamide (0.562 g, 1.5 mmol) in dimethylformamide dimethyl acetal was heated to 120° C. for 11/2 h then cooled and concentrated. The residue was dissolved in acetic acid (4 ml) and hydrazine hydrate (1.1 eq) added. After 11/2 h at 100° C. the solution was cooled, diluted with ethyl acetate and washed with water (×2) and sodium bicarbonate solution. After the solution was dried and concentrated the residue was chromatographed (methanol/dichloromethane) to give the product as a white solid m.p.=127°-129° C.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in acetic acid (4 ml)
  4. washwashed with water (×2) and sodium bicarbonate solution
  5. customAfter the solution was dried
  6. concentrationconcentrated the residue
  7. customwas chromatographed (methanol/dichloromethane)

Sources & evidence

ORD record
ord-608448a966d34bb68a85189c8f9b3343
Source dataset
uspto-grants-1998_10
Patent number
US05827865

Reaction notes

Loading…