Hydrazine hydrate (1:1) → HCID 178467510, compound

HRID 1532028Notes

Reaction equation

HRID 1532028 reaction equation
O.[NH2:2]N.C[N:5]([CH:7]=[N:8][C:9]([C:11]1[O:15][N:14]=[C:13]([O:16][CH2:17][CH3:18])[C:12]=1[CH3:19])=O)C>C(O)(=O)C>[CH2:17]([O:16][C:13]1[C:12]([CH3:19])=[C:11]([C:9]2[N:8]=[CH:7][NH:5][N:2]=2)[O:15][N:14]=1)[CH3:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10823069HCID 10823069, compound

Product 1

HCID 178467510HCID 178467510, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of hydrazine hydrate (0.6 mL, 12.4 mmol) in acetic acid (15 mL) was added N-(dimethylamino)methylidene 3-ethoxy-4-methylisoxazole-5-carboxamide (1.8 g, 8.0 mmol). The reaction mixture was stirred at 90° C. for 15 min and then left at room temperature to crystallize affording pure title compound (1.2 g, 77%): mp 194-196° C. Water was added (40 mL) and the aqueous phase was extracted with EtOAc (3×30 mL). The organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give crude title compound (0.3 g, 20%). The two crops were combined.

Workup

  1. waitleft at room temperature
  2. customto crystallize

Sources & evidence

ORD record
ord-57a7a7db34bd4589b060cbacd1d36bf8
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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