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Dichloromethane → 2,4-Bis(2-acetoxybenzamido)benzoic acid

HRID 1606644
Notes
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Reaction equation

HRID 1606644 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]([O-:15])(=[O:14])[CH3:13].[Na+].C(Cl)Cl.[C:20]([O:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27])(=[O:22])[CH3:21]>O>[C:12]([O:15][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:1][C:2]1[CH:10]=[C:9]([NH:11][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[O:23][C:20](=[O:22])[CH3:21])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:5])(=[O:14])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 691342,4-Diaminobenzoic acidHCID 796682-Acetoxybenzoyl chlorideHCID 517045Sodium Acetate

Product 1

HCID 1913152,4-Bis(2-acetoxybenzamido)benzoic acidYield 97.8%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a mixture of 4.9 g of 2,4-diaminobenzoic acid, 12 g of sodium acetate, 90 ml of methylene chloride and 90 ml of water was added 19.2 g of 2-acetoxybenzoylchloride while stirring at 5° - 10°C, followed by continuing the stirring at 5° - 15°C for 4 hours. The precipitated crystals were recovered by filtration, washed with water and then with methylene chloride and thoroughly mixed with 70 ml of methanol. To the mixture was added 30 ml of water, followed by allowing to stand to precipitate crystals. The crystals were recovered by filtration and recrystallized from 90% aqueous methanol to obtain 7.5 g of 2,4-bis(2'-acetoxybenzamido)-benzoic acid having a melting point between 194° - 195°C.

Workup

  1. customstirring at 5° - 15°C
  2. customfor 4 hours
  3. filtrationThe precipitated crystals were recovered by filtration
  4. washwashed with water
  5. additionwith methylene chloride and thoroughly mixed with 70 ml of methanol
  6. additionTo the mixture was added 30 ml of water
  7. customto precipitate crystals
  8. filtrationThe crystals were recovered by filtration
  9. customrecrystallized from 90% aqueous methanol

Sources & evidence

ORD record
ord-3df42ba8bb434d068dcf99019f2cd26c
Source dataset
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03953496

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes