Dimethylamine → HCID 13881297, compound

HRID 231577Notes

Reaction equation

HRID 231577 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:9]=1[C:10]([O:12]C)=O)(=[O:7])=[O:6].[CH3:21][NH:22][CH3:23].CC(C)([O-])C.[K+]>CO.C(O)(C)(C)C>[CH3:21][N:22]([CH3:23])[C:10](=[O:12])[C:9]1[C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=[CH:17][C:8]=1[S:5]([NH:4][CH2:3][CH2:2][OH:1])(=[O:6])=[O:7]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 13881293HCID 13881293, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13881297HCID 13881297, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6386tert-ButanolSolvent

Procedure

A solution of methyl 2-[N-(2-hydroxyethyl)aminosulfonyl]-6-nitrobenzoate (4.58 g, 15.1 mmol) in absolute MeOH (50 ml) was added to a solution of dimethylamine (6.8 g, 0.15 mol) and potassium tertbutoxide (0.68 ml of a 0.262 M soluton in tertbutanol) in absolute MeOH (100 ml). After stirring at 20-25° for 4 days, solvents were removed under reduced pressure. The residue was dissolved in EtOAc and washed with 0.5N HCl followed by a saturated aqueous NaCl solution. The EtOAc extract was dried (Na2SO4), filtered and concentrated to give 4.2 g (88%) of product.

Workup

  1. customsolvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 0.5N HCl
  4. extractionThe EtOAc extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f719d29beeae4c14b8c70bc0d7cb9b1f
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

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