Acetic Anhydride → HCID 23458908, compound

HRID 1680048Notes

Reaction equation

HRID 1680048 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O.O>[CH2:15]([O:14][C:12]([C:11]1[CH:17]=[CH:18][C:8]([N:7]([CH2:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:21](=[O:23])[CH3:22])=[CH:9][CH:10]=1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 773384Benzoic acid, 4-[[(4-chlorophenyl)methyl]amino]-, ethyl ester

Product 1

HCID 23458908HCID 23458908, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

Ethyl 4-(4-chlorobenzylamino)-benzoate (11.56 g; 0.04 M), acetic anhydride (40 ml) and concentrated sulphuric acid (5 drops) were mixed and heated with stirring on a steam-bath for 1 hour. The mixture was cooled to room temperature, added to iced water (100 ml) and neutralised with solid sodium bicarbonate. The product was extracted into dichloromethane (2×100 ml), washed with water (1×100 ml) and evaporated to give an oil from which N-(4-ethoxycarbonylphenyl)-N-(4-chlorobenzyl)-acetamide (8.32 g; 63%) was obtained by chromatography on silica-gel in dichloromethane then 2% methanol-dichloromethane followed by crystallisation from ethanol. M.p. 65°-6° C.

Workup

  1. temperatureheated
  2. extractionThe product was extracted into dichloromethane (2×100 ml)
  3. washwashed with water (1×100 ml)
  4. customevaporated

Sources & evidence

ORD record
ord-7aa6d29ddb1740e9a9087249cee9ec62
Source dataset
uspto-grants-1981_06
Patent number
US04271188

Reaction notes

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