N,N-Dimethylethylenediamine → HCID 13785476, compound

HRID 231572Notes

Reaction equation

HRID 231572 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([O:9]C)=[O:8])(=[O:4])=[O:3].[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22]>C1COCC1>[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH:22][S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([OH:9])=[O:8])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoate

Product 1

HCID 13785476HCID 13785476, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-chlorosulfonyl-6-nitrobenzoate (500 mg, 1.79 mmol) and 2-dimethylaminoethylamine (316 mg, 3.58 mmol) in THF (35 ml) was stirred in an ice bath for 1 hour then at 20-25° for 18 hours. After removing THF under reduced pressure, the residue was partitioned between saturated Na2CO3 solution and EtOAc. The organic extract was washed (saturated NaCl solution), dried (Na2SO4), filtered and concentrated under reduced pressure. Chromatography over silica gel (elution with 5% MeOH-95% CHCl3) gave an oil which when triturated with EtOAc afforded 2-[N-(2-dimethylaminoethyl)aminosulfonyl]-6-nitrobenzoic acid (90 mg, 16%), m.p. 193° decomposed with effervescence.

Workup

  1. customAfter removing THF under reduced pressure
  2. customthe residue was partitioned between saturated Na2CO3 solution and EtOAc
  3. extractionThe organic extract
  4. washwas washed (saturated NaCl solution)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customChromatography over silica gel (elution with 5% MeOH-95% CHCl3) gave an oil which when
  9. customtriturated with EtOAc

Sources & evidence

ORD record
ord-aa68a4fbf6724d968932fddefe6b29c9
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

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