Hydrochloric Acid → HCID 13485039, compound

HRID 1953037Notes

Reaction equation

HRID 1953037 reaction equation
C([O:3][C:4](=[O:24])[C:5]([NH:20]C(=O)C)([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)C(OCC)=O)C.C(NC(C(OCC)=O)C(OCC)=O)(=O)C.BrCC1C=CC(C#N)=CC=1.[O-]CC.[Na+].[ClH:54]>C(O)(=O)C>[ClH:54].[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH:5]([C:4]([OH:24])=[O:3])[NH2:20])=[CH:17][CH:16]=1)#[N:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14041Acetamidomalonic acid diethyl esterHCID 869964-(Bromomethyl)benzonitrileHCID 640014propanedioic acid, (acetylamino)[(4-cyanophenyl)methyl]-, diethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 13485039HCID 13485039, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 235 g (0.707 Mol) of diethyl -(acetamido)-α-[(4-cyanophenyl)methyl]-malonate (Mp. 163-165° C.; prepared from diethyl α-(acetamido)-malonate and 4-(bromomethyl)-benzonitrile in the presence of sodium ethoxide), 1.28 l (3.84 Mol) of 3N aqueous hydrochloric acid and 0.64 l of glacial acetic acid were refluxed for 7 hours. The mixture cooled to +5° C. was filtered and the filtrate was evaporated down in vacuo. The residue was intensively washed with isopropanol and then dried in vacuo. 92.9 g (58% of theory) of colourless crystals were obtained, Mp. 219° C. (D.).

Workup

  1. temperaturewere refluxed for 7 hours
  2. temperatureThe mixture cooled to +5° C.
  3. filtrationwas filtered
  4. customthe filtrate was evaporated down in vacuo
  5. washThe residue was intensively washed with isopropanol
  6. customdried in vacuo
  7. custom92.9 g (58% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-826791948acb4e878837e7b15171284f
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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