Dimethylamine → HCID 13881297, compound

HRID 1906908Notes

Reaction equation

HRID 1906908 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>[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

5

Reactant 3

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

Product 1

HCID 13881297HCID 13881297, compoundYield 88%

Reagents, catalysts & solvents 1

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 solution in tertbutanol) in absolute MeoH (100 ml). After stirring at 20°-25° C. 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-4d5188af0cd049a1809b7421165961a1
Source dataset
uspto-grants-1987_03
Patent number
US04654369

Reaction notes

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