Benzenesulfonyl chloride, 2,4-dinitro- → HCID 69666587, compound

HRID 379254Notes

Reaction equation

HRID 379254 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C@@H:6]([C:8]1[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)[NH2:7])[CH3:2].C([O-])(O)=O.[Na+].[N+]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[S:34](Cl)(=[O:36])=[O:35])([O-])=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C@@H:6]([C:8]1[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)[NH:7][S:34]([C:26]1[CH:25]=[CH:30][C:29]([N+:31]([O-:33])=[O:32])=[CH:28][CH:27]=1)(=[O:35])=[O:36])[CH3:2]

Participants

5

Reactant 3

HCID 74255Benzenesulfonyl chloride, 2,4-dinitro-HCID 516892Sodium BicarbonateHCID 10977104HCID 10977104, compound

Product 1

HCID 69666587HCID 69666587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of aminoester 16-5 (3.0 g, 13.0 mmol) in CH2Cl2 (20 mL) was treated with aq NaHCO3 (4.4 g in 20 mL H2O). 2,4-Dinitrobenzenesulfonyl chloride (4.3 g, 16 mmol) was added and the reaction mixture stirred for 12 h. The solution was extracted with CH2Cl2 (3×40 mL) and the combined organic solutions washed with satd aq NaHCO3 (40 mL) and brine (40 mL). The solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (97:3 CH2Cl2/MeOH) to give the desired product 16-6.

Workup

  1. extractionThe solution was extracted with CH2Cl2 (3×40 mL)
  2. washthe combined organic solutions washed with satd aq NaHCO3 (40 mL) and brine (40 mL)
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (97:3 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-88113bdad42046f5aab88c60927fdfc3
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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