Hydrochloric Acid → Benzamide, 2-(benzoyloxy)-N-(4-(benzoyloxy)-3,5-dichlorophenyl)-

HRID 1282947Notes

Reaction equation

HRID 1282947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:19])[C:17]=1[OH:18])[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>N1C=CC=CC=1>[C:20]([O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]([NH:5][C:4]1[CH:3]=[C:2]([Cl:1])[C:17]([O:18][C:6](=[O:14])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:16]([Cl:19])[CH:15]=1)=[O:14])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 10424739HCID 10424739, compound

Product 1

HCID 3043339Benzamide, 2-(benzoyloxy)-N-(4-(benzoyloxy)-3,5-dichlorophenyl)-Yield 88.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3',5'-Dichloro-2,4'-dihydroxybenzanilide (1 g.) was dissolved in dry pyridine (15 ml.) in the cold at 0°- 5° C. and to it was added dropwise benzoyl chloride (1.2 ml.). With gentle stirring reaction was continued for several hours. The solution was then poured into ice-cold water and acidified with 1 N hydrochloric acid to pH 2, yielding oily material which was extracted by ethyl acetate. The ethyl acetate solution was washed with 1 N hydrochloric acid and 5% sodium bicarbonate solution in that order and dried with anhydrous sodium sulfate, followed by removal of the solvent by evaporation. The residue was subjected to recrystallization from ether and petroleum ether mixture to give white crystals (1.5 g.) of 2,4'-dibenzoyloxy-3',5'-dichlorobenzanilide. Yield: 88.2%. Melting point: 157°-160° C.

Workup

  1. customreaction
  2. waitwas continued for several hours
  3. additionThe solution was then poured into ice-cold water
  4. customyielding oily material which
  5. extractionwas extracted by ethyl acetate
  6. washThe ethyl acetate solution was washed with 1 N hydrochloric acid and 5% sodium bicarbonate solution in that order
  7. dry with materialdried with anhydrous sodium sulfate
  8. customfollowed by removal of the solvent by evaporation
  9. customThe residue was subjected to recrystallization from ether and petroleum ether mixture

Sources & evidence

ORD record
ord-d02f8d5cd56b4eb1827fed8f2103a123
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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