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Benzoyl chloride → N-[4-(3,5-dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl]benzamide

HRID 1062635
Notes
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Reaction equation

HRID 1062635 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([NH2:20])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([NH:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 9925734[4-(3,5-Dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl)amine

Product 1

HCID 22282227N-[4-(3,5-dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl]benzamideYield 26%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridine
Catalyst
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [4-(3,5-dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl]amine (0.51 g, 1.8 mmol) and 4-dimethylaminopyridine (0.06 g, 0.52 mmol) in N,N-dimethylacetamide (20 mL) was added benzoyl chloride (0.30 g, 2.15 mmol) and the mixture was stirred at 80° C. for 14 h. To the reaction mixture was poured aqueous sodium hydrogencarbonate solution and the precipitated solid was collected by filtration. The obtained solid was washed with water and dried. The crude crystals were recrystallized from ethanol to give the title compound (0.18 g, yield 26%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe obtained solid was washed with water
  3. customdried
  4. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-d747c79a46b2415f93d1d5bd6ec6dbbd
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06962933B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes