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Triethylamine → N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide

HRID 541829
Notes
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Reaction equation

HRID 541829 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([Cl:31])=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CN(C=O)C>[Cl:23][C:24]1[N:29]=[C:28]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][S:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=2)[C:27]([Cl:31])=[CH:26][N:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66881065N-(3-Aminophenyl)-1-(3-nitrophenyl)methanesulfonamide Hydrochloride

Product 1

HCID 86636268N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamideYield 60.7%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-aminophenyl)-1-(3-nitrophenyl)methanesulfonamide-hydrogen chloride (0.10 g, 0.29 mmol) and 2,4,5-trichloropyrimidine (0.065 g, 0.35 mmol) in DMF (1 mL) was added potassium carbonate (0.20 g, 1.4 mmol). The resulting mixture was stirred overnight at room temperature. Additional triethylamine (0.099 mL, 0.71 mmol) was added and stirred again overnight. The reaction was then quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous phase was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The crude was purified by column chromatography to give the desired product (0.080 g, 60%). LCMS for C17H13Cl2N5O4S (M+H)+: m/z=453.9, 455.9.

Workup

  1. stirringstirred again overnight
  2. customThe reaction was then quenched with sat'd NH4Cl and water
  3. additionEtOAc was added
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted with EtOAc
  6. washThe combined organics were washed with water and brine
  7. dry with materialthen dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-0b20f03c7f0c4902ba47c684a3307e39
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871753B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes