Water → HCID 23458906, compound

HRID 1680045Notes

Reaction equation

HRID 1680045 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])C.O.C(=O)(O)[O-].[Na+]>C(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)[CH:21]=[O:23])=[CH:9][CH:10]=1)=[O:13])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 773384Benzoic acid, 4-[[(4-chlorophenyl)methyl]amino]-, ethyl ester

Product 1

HCID 23458906HCID 23458906, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
55 °C

Procedure

Ethyl 4-(4-chlorobenzylamino)-benzoate (7.2 g; 0.025 mole) was dissolved in formic acid (80%; 70 ml) and the solution was heated to 55° C. with stirring. Acetic anhydride (25 ml) was added dropwise at this temperature, allowed to cool to room temperature and stirred for 1 hour. The reaction mixture was added to iced water (100 ml) and the aqueous mixture was neutralised with solid sodium bicarbonate. The product was extracted into dichloromethane (2×100 ml), washed with water (1×100 ml), dried (anhydrous MgSO4) and evaporated. Pure N-(4-ethoxycarbonylphenyl)-N-(4-chlorobenzyl)-formamide (5.32 g; 67%) was obtained by chromatography on silica-gel in dichloromethane followed by crystallisation from ethanol. M.p. 72°-3° C.

Workup

  1. temperatureto cool to room temperature
  2. stirringstirred for 1 hour
  3. extractionThe product was extracted into dichloromethane (2×100 ml)
  4. washwashed with water (1×100 ml)
  5. dry with materialdried (anhydrous MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0d60593796ec45afa408be4877cb39db
Source dataset
uspto-grants-1981_06
Patent number
US04271188

Reaction notes

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