Acetic Anhydride → HCID 178469637, compound

HRID 1168521Notes

Reaction equation

HRID 1168521 reaction equation
[OH:1][CH2:2][C:3]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:4]=1[NH:5][CH:6]=[C:7]([C:13]([O:15]CC)=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([O:1][CH2:2][C:3]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]2[C:4]=1[N:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:13]2[OH:15])(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 12083046HCID 12083046, compound

Product 1

HCID 178469637HCID 178469637, compound

Conditions

Temperature
130 °C

Procedure

A mixture of diethyl 2-((2-(hydroxymethyl)-4-methylanilino)methylene)malonate (Preparation 24, 5.0 g) and acetic anhydride (5.0 mL) is heated at 130° C. for 1 h. The acetic anhydride is evaporated, and the residual solid is heated at reflux in diphenyl ether (20 ml) for 1 h. The solution is cooled and diluted with acetonitrile (5 mL) and ether (15 mL). The resulting precipitate is filtered to afford 1.8 g of the title compound.

Workup

  1. customThe acetic anhydride is evaporated
  2. temperaturethe residual solid is heated
  3. temperatureat reflux in diphenyl ether (20 ml) for 1 h
  4. temperatureThe solution is cooled
  5. additiondiluted with acetonitrile (5 mL) and ether (15 mL)
  6. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-e2ba29b6f45d4360908fff906e9afb7c
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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