Ethyl benzoylacetate → HCID 18980359, compound

HRID 2392708Notes

Reaction equation

HRID 2392708 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([CH2:21][C:22](OCC)=[O:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)(Cl)Cl>[C:13]([CH2:21][C:22]([NH:6][C:5]1[CH:7]=[C:8]([Cl:9])[C:2]([Cl:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11])=[O:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 18980359HCID 18980359, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4,5-dichloro-2-nitroaniline (2.07 g, 10 mmol) and ethyl benzoylacetate (technical, 5 mL, approximately 22 mmol) was heated at 180° C. for 16 h under stirring. It was cooled to 150° C. and kept at this temperature under aspirator vacuum for 5 h, then cooled to room temperature. Chloroform (50 mL) was added and the mixture was evaporated, then diluted with ether (200 mL) and cooled to -10° C. Precipitate was filtered and washed with ether (5×50 mL) to give 2.12 g (60%) of the title compound as an orange solid: mp 177°-179° C. (from EtOH); IR (KBr) 3330, 1693, 1670, 1561, 1472, 1340, 1233, and 764 cm-1 ; 1H NMR (DMSO-d6) δ4.24 (s, 2H), 7.53 (m, 2H), 7.65 (m, 1H), 7.77 (d, 1H, J=7.6 Hz), 7.97 (d, 1H, J=7.6 Hz), 8.11 (s, 1H), 8.23 (s, 1H), 10.70 (s, 1H, N--H). HRMS Calcd for C15H10N2O4Cl2 : 352.0018. Found: 352.0020.

Workup

  1. temperatureIt was cooled to 150° C.
  2. temperaturecooled to room temperature
  3. customthe mixture was evaporated
  4. additiondiluted with ether (200 mL)
  5. temperaturecooled to -10° C
  6. filtrationPrecipitate was filtered
  7. washwashed with ether (5×50 mL)

Sources & evidence

ORD record
ord-f03e24c0fbda47fcb19f81971fb91867
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

Loading…