Water → HCID 68540518, compound

HRID 2243467Notes

Reaction equation

HRID 2243467 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[CH3:5][C:6]1[C:7]([N+:16]([O-:18])=[O:17])=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1.O>ClCCl>[CH3:5][C:6]1[C:7]([N+:16]([O-:18])=[O:17])=[C:8]([S:12]([NH:4][CH:1]([CH3:3])[CH3:2])(=[O:13])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6363IsopropylamineHCID 1226789660310-10-3

Product 1

HCID 68540518HCID 68540518, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isopropylamine (13 mL, 155 mmol) in 60 mL of dichloromethane at 0° C. was added a solution of 5.3 g of 3-methyl-2-nitrobenzenesulfonyl chloride (prepared according to Courtin, A. Helv. Chim. Acta, 1976, 59, 379-387) in 60 mL of dichloromethane dropwise. The reaction mixture was stirred 2 hours at room temperature. Water was added and the layers were separated. The organic layer was dried (sodium sulfate) and the volatiles were removed with a rotary evaporator. The residue was purified by medium pressure liquid chromatography (MPLC), using 20-40% ethyl acetate in hexanes as eluant, to afford 4.3 g of the title compound as a yellow solid.

Workup

  1. customprepared
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customthe volatiles were removed with a rotary evaporator
  5. customThe residue was purified by medium pressure liquid chromatography (MPLC)

Sources & evidence

ORD record
ord-5f9ffcfcfb8643718b19fd524897d587
Source dataset
uspto-grants-2010_03
Patent number
US07674936B2

Reaction notes

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