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

HRID 1004274Notes

Reaction equation

HRID 1004274 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-40ad46738c8d45708fa63d90b43439c2
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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