Acetic Acid → Isopropyl 2-[N-(2-Dimethylaminoethyl)aminosulfonyl]-6-nitrobenzoate Hydrochloride

HRID 231583Notes

Reaction equation

HRID 231583 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:23])[CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:11]=1[C:12](OC)=[O:13])(=[O:9])=[O:8].[CH3:24][CH:25]([CH3:27])[O-:26].[Na+].C(O)(=O)C>C(O)(C)C>[ClH:1].[CH3:2][N:3]([CH3:23])[CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:11]=1[C:12]([O:26][CH:25]([CH3:27])[CH3:24])=[O:13])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 109204432-Propanol, sodium salt (1:1)HCID 20033752methyl 2-[N-(2-dimethylaminoethyl)aminosulfonyl]-6-nitrobenzoate hydrochloride

Product 1

HCID 20033755Isopropyl 2-[N-(2-Dimethylaminoethyl)aminosulfonyl]-6-nitrobenzoate HydrochlorideYield 31%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of methyl 2-[N-(2-dimethylaminoethyl)aminosulfonyl]-6-nitrobenzoate hydrochloride (12.0 g, 32.6 mmol) in dry isopropanol (500 mL) containing sodium isopropoxide (39 mmol) was stirred at reflux under N2 for 18 hours. After adding glacial acetic acid (1 mL) and concentrating under reduced pressure, the residue was partitioned between ethyl acetate and water. The ethyl acetate extract was washed with a saturated aqueous solution of sodium chloride, dried (Na2SO4), filtered and concentrated. The residue was converted to the hydrochloride salt with ethanolic anhydrous hydrogen chloride and recrystallized from methanol - ethyl acetate to give 4.0 g (31%) of product, m.p. 187.0-190.0° dec. Anal Calc'd for C14H21N3O6S.HCl: C, 42.47; H, 5.60; N, 10.61

Workup

  1. temperatureat reflux under N2 for 18 hours
  2. concentrationconcentrating under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe ethyl acetate extract
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customrecrystallized from methanol - ethyl acetate

Sources & evidence

ORD record
ord-b4096657a1be4e7885a9aa2e6871eaf0
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

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