Toluene → HCID 21442848, compound

HRID 1606511Notes

Reaction equation

HRID 1606511 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:17]12[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=1)[NH:22]C(=O)O[C:18]2=[O:19].C1(C)C=CC=CC=1>CCOCC>[C:18]([O:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:13][CH2:12]1)(=[O:19])[C:17]1[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=1)[NH2:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8359Isatoic AnhydrideHCID 967031-Piperazineethanol, 4-(3-chlorophenyl)-

Product 1

HCID 21442848HCID 21442848, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7.2 G. (0.03 mol) of 2-(4-m-chlorophenyl-piperazino)-ethanol and 6.55 g. (0.04 mol) of isatoic anhydride in 125 ml. of toluene are refluxed for 3 hours. The hot toluene solution is filtered and the toluene is evaporated from the filtrate to give a residue which is taken up in ether in order to remove a small amount of unreacted isatoic anhydride, the solution is filtered and the ether is driven off. The remaining product is triturated in petroleum ether, filtered off and recrystallised twice from isopropyl alcohol to give 7.6 g. (yield = 70%) of 2-(4-m-chlorophenylpiperazino)-ethyl anthranilate, which melts at 76°C.

Workup

  1. filtrationThe hot toluene solution is filtered
  2. customthe toluene is evaporated from the filtrate
  3. customto give a residue which
  4. customto remove a small amount of unreacted isatoic anhydride
  5. filtrationthe solution is filtered
  6. customThe remaining product is triturated in petroleum ether
  7. filtrationfiltered off
  8. customrecrystallised twice from isopropyl alcohol
  9. customto give 7.6 g

Sources & evidence

ORD record
ord-3b06104217764322b5bb29aebb5a013c
Source dataset
uspto-grants-1976_04
Patent number
US03953449

Reaction notes

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