Potassium Carbonate → HCID 57961833, compound

HRID 541820Notes

Reaction equation

HRID 541820 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([Cl:29])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:21][C:22]1[N:27]=[C:26]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=2)[C:25]([Cl:29])=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 43602671HCID 43602671, compound

Product 1

HCID 57961833HCID 57961833, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-aminophenyl)-3-nitrobenzenesulfonamide (1.00 g, 3.41 mmol) and 2,4,5-trichloropyrimidine (0.57 g, 3.1 mmol) in DMF (10 mL) was added potassium carbonate (0.52 g, 3.7 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The crude was purified by combi-flash column chromatography to give the desired product (1.2 g, 88%). LCMS for C16H11Cl2N5O4S (M+H)+: m/z=439.9, 441.9. 1H NMR (400 MHz, DMSO-d6): δ 10.65 (s, 1H), 9.51 (s, 1H), 8.54 (t, J=2.1 Hz, 1H), 8.43 (ddd, J=8.2, 2.0, 1.0 Hz, 1H), 8.37 (s, 1H), 8.18 (ddd, J=8.0, 2.0, 1.0 Hz, 1H), 7.84 (t, J=8.0 Hz, 1H), 7.50 (t, J=2.0 Hz, 1H), 7.29 (ddd, J=8.2, 2.0, 1.2 Hz, 1H), 7.24 (m, 1H), 6.88 (ddd, J=8.0, 2.0, 1.2 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-6182abf1eec74bf184d29ab667b7dc8c
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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