Formic Acid → HCID 23128148, compound

HRID 358687Notes

Reaction equation

HRID 358687 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[CH2:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[CH3:21])[CH3:12].[OH-].[Na+]>O>[C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:13]([CH2:11][CH3:12])[CH:8]=[O:10])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 13213874HCID 13213874, compound

Product 1

HCID 23128148HCID 23128148, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic anhydride (23 ml) and formic acid (15.5 ml) was stirred at 50° for 4 hours and then cooled to 0° in an ice/salt bath. 2'-(Ethylamino)-acetophenone (20.5 g) was added in small portions over 15 minutes and the mixture allowed to stand at room temperature for 1 hour. The mixture was cooled to 0° and water (100 ml) followed by aqueous sodium hydroxide (specific gravity 1.5, 10 ml) was added dropwise whilst maintaining the temperature below 10°. The resultant mixture was extracted with dichloromethane (4×100 ml) and the combined extracts were dried over magnesium sulphate to give a solution of 2'-acetyl-N-ethylformanilide.

Workup

  1. temperaturecooled to 0° in an ice/salt bath
  2. waitto stand at room temperature for 1 hour
  3. temperatureThe mixture was cooled to 0°
  4. additionwas added dropwise
  5. temperaturewhilst maintaining the temperature below 10°
  6. extractionThe resultant mixture was extracted with dichloromethane (4×100 ml)
  7. dry with materialthe combined extracts were dried over magnesium sulphate

Sources & evidence

ORD record
ord-37d7a1a6c15d46af9e2e59d35d65eb17
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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