Hydrazine hydrate (1:1) → HCID 135738336, compound

HRID 1270297

Reaction equation

HRID 1270297 reaction equation
O.[NH2:2]N.Cl.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[NH:16])[NH2:15])=[CH:10][CH:9]=1)([O-:7])=[O:6].[C:17]([NH:20][CH:21]([CH3:29])[C:22](=O)[C:23](OCC)=[O:24])(=[O:19])[CH3:18]>C(O)C>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[NH:15][C:23](=[O:24])[C:22]([CH:21]([NH:20][C:17](=[O:19])[CH3:18])[CH3:29])=[N:2][N:16]=2)=[CH:12][CH:13]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 1706254-Nitrobenzamidine hydrochlorideHCID 22245807Ethyl 3-acetamido-2-oxobutanoate

Product 1

HCID 135738336HCID 135738336, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

7.30 g (7.09 ml, 145.82 mmol) of hydrazine hydrate are added dropwise to 24.50 g (121.5 mmol) of 4-nitrobenzenecarboximidamide hydrochloride from example 1A are in 250 ml of ethanol. The mixture is stirred for one hour at 20° C. After this time, 34.12 g (182.28 mmol) of ethyl 3-(acetylamino)-2-oxobutanoate from example 4A are added in ethanol, and the reaction mixture is stirred for 4 h at a bath temperature of 70–80° C., subsequently for 12 h at 20° C. The mixture is concentrated and the residue is purified by flash chromatography (eluent: ethyl acetate, subsequently dichloromethane/methanol 30:1).

Workup

  1. stirringthe reaction mixture is stirred for 4 h at a bath temperature of 70–80° C.
  2. waitsubsequently for 12 h at 20° C
  3. concentrationThe mixture is concentrated
  4. customthe residue is purified by flash chromatography (eluent

Sources & evidence

ORD record
ord-32ae0f887b1a4abbbf38df4bcbecd908
Source dataset
uspto-grants-2007_04
Patent number
US07202243B2

Linked notes

Loading…