Dimethylamine → HCID 13881297, compound

HRID 2309210Notes

Reaction equation

HRID 2309210 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+]>C(O)(C)(C)C.CO>[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 887MethanolSolventHCID 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 solution 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 0.5 N 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 0.5 N HCl
  4. extractionThe EtOAc extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bd022c0a0cc040fe872dd85d84af9d07
Source dataset
uspto-grants-1987_09
Patent number
US04694020

Reaction notes

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