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Triethylamine → Methyl 3-[(4-methoxybenzoyl)amino]-4-[(4-tert-butylbenzoyl)amino]benzoate

HRID 395798
Notes
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Reaction equation

HRID 395798 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[NH2:20])[C:13]([O:15][CH3:16])=[O:14])=[O:8])=[CH:5][CH:4]=1.C(#N)C.C(Cl)(Cl)Cl.C(N(CC)CC)C.[C:37]([C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1)([CH3:40])([CH3:39])[CH3:38]>C(#N)C>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[NH:20][C:45](=[O:46])[C:44]2[CH:48]=[CH:49][C:41]([C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:42][CH:43]=2)[C:13]([O:15][CH3:16])=[O:14])=[O:8])=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 10732961Methyl 4-amino-3-(4-methoxybenzamido)benzoateHCID 22555007Acetonitrile chloroform

Product 1

HCID 10742629Methyl 3-[(4-methoxybenzoyl)amino]-4-[(4-tert-butylbenzoyl)amino]benzoateYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 3-[(4-methoxybenzoyl)amino]-4-aminobenzoate (0.800 g, 2.67 mmol) in 1:1 acetonitrile/chloroform (100 mL) was cooled to 0° C. and treated with triethylamine (0.41 mL, 2.9 mmol), and a solution of 4-tert-butylbenzoyl chloride (0.58 mL) in acetonitrile (25 μL). The reaction mixture was allowed to warm to room temperature over 16 h, concentrated in vacuo, diluted with ethyl acetate, washed with cold dilute aqueous hydrochloric acid and cold saturated aqueous sodium bicarbonate solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Crystallization of the residue from methylene chloride/hexane provided 1.0 g (81%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with cold dilute aqueous hydrochloric acid and cold saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customCrystallization of the residue from methylene chloride/hexane

Sources & evidence

ORD record
ord-c33f813b740a4c058244aab64be9211f
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06605626B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes