Sodium Chloride → HCID 17986362, compound

HRID 970422Notes

Reaction equation

HRID 970422 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)(=[O:8])=[O:7].[H-].[Na+].[Br:20][C:21]1[C:22](Cl)=[N:23][C:24]([Cl:27])=[N:25][CH:26]=1.[Na+].[Cl-]>CN(C=O)C>[Br:20][C:21]1[C:22]([O:1][CH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)(=[O:7])=[O:8])=[N:23][C:24]([Cl:27])=[N:25][CH:26]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 17986391HCID 17986391, compound

Product 1

HCID 17986362HCID 17986362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 272 mg (1.05 mmol) of N-(3-hydroxy-propyl)-3-nitro-benzenesulfonamid in 5 ml DMF is mixed with 49 mg of a 60% dispersion of sodium hydride in mineral oil (1.22 mmol) and stirred for 5 minutes at room temperature. It is mixed with a solution of 220 mg (0.97 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 5 ml of DMF and stirred for another 2 hours. The batch is mixed with saturated NaCl solution and then extracted with ethyl acetate (2×). The combined organic phases are washed with NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 1:1, Flashmaster II). 75 mg (0.16 mmol, corresponding to 16% of theory) of the product is obtained.

Workup

  1. stirringstirred for another 2 hours
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic phases are washed with NaCl solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe remaining residue is purified by chromatography (hexane/ethyl acetate 1:1, Flashmaster II)
  8. custom75 mg (0.16 mmol, corresponding to 16% of theory) of the product is obtained

Sources & evidence

ORD record
ord-57963eb1aec84c1b975ada2cc9e98165
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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