Toluene → HCID 11116961, compound

HRID 1030508Notes

Reaction equation

HRID 1030508 reaction equation
[CH:1]1([C:4](=[N:6][OH:7])[NH2:5])[CH2:3][CH2:2]1.[C:8]1(C)C=CC=C[CH:9]=1.C([C:17]([CH2:24]C)([C:21]([O-:23])=[O:22])C([O-])=O)C>C(O)C.O>[CH2:8]([O:23][C:21](=[O:22])[CH2:17][C:24]1[O:7][N:6]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[N:5]=1)[CH3:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 11116961HCID 11116961, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A 20 gallon glass-lined vessel was charged with cyclopropylcarboxamide oxime (5) (5.39 kg, 53.9 Mol), toluene (Shell Chem, 324, 54.0 l) and diethylmalonate (Lancaster B/N 52068785, 24.5 kg, 160 Mol) under nitrogen at room temperature. The stirred reaction mixture was heated at gentle reflux for 21 h. The ethanol/water produced during the reaction was periodically drawn off to maintain a high reflux temperature (i.e 105°-110° C.). The reaction mixture was cooled to room temperature, washed with 25% saturated brine (3×5 l) and the toluene removed under reduced pressure. The residue was distilled using a small fractionating column to give: a) recovered diethylmalonate b.p. 60°-70° C. at 2 mbar; and b) oxadiazole-ester (6) b.p. 90°-120° C., at ~ 2 mbar.

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureat gentle reflux for 21 h
  4. temperatureto maintain a high reflux temperature (i.e 105°-110° C.)
  5. washwashed with 25% saturated brine (3×5 l)
  6. customthe toluene removed under reduced pressure
  7. distillationThe residue was distilled
  8. customto give
  9. customa) recovered diethylmalonate b.p. 60°-70° C. at 2 mbar

Sources & evidence

ORD record
ord-34e719207a064ed384a547fbcbc3216b
Source dataset
uspto-grants-1992_04
Patent number
US05106853

Reaction notes

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