1,2-Dichloroethane → HCID 53730667, compound

HRID 1418054Notes

Reaction equation

HRID 1418054 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:13][NH:14][O:15][CH3:16].CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:6]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14912,4-Dihydroxybenzoic AcidHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 53730667HCID 53730667, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 2,4-dihydroxybenzoic acid (8 g, 52 mmol), N,O-dimethylhydroxylamine hydrochloride (6.1 g, 62 mmol) and N-methylmorpholine (13.18 g, 130 mmol) in methylene chloride (50 mL) at 0° C. was added EDC batchwise (11.95 g, 62.3 mmol). Stirred at room temperature for 3 days. The reaction was quenched by the addition of water and then extracted with methylene chloride (2 times). The combined organic extracts were successively washed with a 10% aqueous citric acid solution, a 5% sodium bicarbonate solution, water and saturated salt solution and dried over anhydrous sodium sulfate. The mixture was filtered and the solvent removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 0-33% ethyl acetate in hexanes to yield the title compound, mass spectrum (CI) m/e=198 (M+1)+.

Workup

  1. customThe reaction was quenched by the addition of water
  2. extractionextracted with methylene chloride (2 times)
  3. washThe combined organic extracts were successively washed with a 10% aqueous citric acid solution
  4. dry with materiala 5% sodium bicarbonate solution, water and saturated salt solution and dried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. customthe solvent removed by rotoevaporation
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluted with 0-33% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-aa55c9ae84cd4112bfbbc777d385261d
Source dataset
uspto-grants-1999_03
Patent number
US05880139

Reaction notes

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