Phthalic Anhydride → HCID 69272449, compound

HRID 2221108Notes

Reaction equation

HRID 2221108 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH3:2].[C:14]1(=O)[O:19][C:17](=[O:18])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[C:16]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]3[C:14]2=[O:19])=[CH:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 12731941Ethyl (4-aminophenyl)carbamate

Product 1

HCID 69272449HCID 69272449, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

(4-Amino-phenyl)-carbamic acid ethyl ester (118 g, 0.65 mol) is dissolved in glacial acetic acid (2.0 L) under nitrogen and the mixture is heated to 90° C. Phthalic anhydride (102.0 g, 0.69 mol) is added portionwise over 30 minutes and the reaction is kept at 90° C. for 2 hours. The mixture is allowed to cool to ambient temperature and the precipitated solid is filtered off. The solid is washed on the filter with water (2 L) followed by diethylether (3 L) and then dried in vacuo. Yield 127 g (62%) title compound as white crystalline compound. LC/MS (m/z) 311.3 (MH+); tR=2.57 min. 1H NMR (DMSO-d6): 1.26 (t, 3H); 4.15 (q, 2H); 7.34 (dd, 2H); 7.58 (dd, 2H); 7.90 (ddd, 2H); 7.95 (ddd, 2H); 9.80 (s, 1H, NH).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationthe precipitated solid is filtered off
  3. washThe solid is washed on the
  4. filtrationfilter with water (2 L)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a27cad8c7661460484fe27a5301cbc38
Source dataset
uspto-grants-2008_05
Patent number
US07368472B2

Reaction notes

Loading…