Benzocaine → HCID 178468800, compound

HRID 2304424Notes

Reaction equation

HRID 2304424 reaction equation
C(OC(=O)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][N:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15])=[CH:7][CH:6]=1)C.NC1C=CC([C:24]([O:26][CH2:27][CH3:28])=[O:25])=CC=1.C(#N)CC#N.O.[NH2:37][NH2:38]>>[CH2:27]([O:26][C:24](=[O:25])[C:7]1[CH:6]=[CH:5][CH:10]=[CH:9][C:8]=1[NH:11][N:12]=[C:13]1[C:14]([NH2:15])=[N:38][N:37]=[C:16]1[NH2:17])[CH3:28]

Participants

5

Reactant 4

HCID 2337BenzocaineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 14902661HCID 14902661, compound

Product 1

HCID 178468800HCID 178468800, compoundYield 33%

Procedure

This compound was prepared using 121 mg (0.5 mmol) of 4-(N′-dicyanomethylene-hydrazino)benzoic acid ethyl ester, which was derived from ethyl 4-aminobenzoate (165 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. The hydrazine hydrate was added to the solution at a temperature of 75° C. The solution cleared briefly and then a precipitate formed. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 45 mg (33%) of the title compound as a yellow solid.

Workup

  1. customThis compound was prepared
  2. customa precipitate formed
  3. customThe resulting solid was isolated by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-e62e1e3a67444f2f89341cb06b61cc5c
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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