Triethylamine → HCID 20186169, compound

HRID 2309279Notes

Reaction equation

HRID 2309279 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][CH2:15][C:16]#[N:17])(=[O:13])=[O:12])([O:3]C)=O.C(N(CC)CC)C.[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30]Cl>ClCCl>[C:16]([C:15]1[N:14]([CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[S:11](=[O:13])(=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:1]=1[OH:3])#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 3503190HCID 3503190, compound

Product 1

HCID 20186169HCID 20186169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of o-carbomethoxy-N-cyanomethylbenzenesulfonamide (6.25 g) in dichloromethane (50 ml) was added triethylamine (2.5 g) and then beta-methoxyethoxymethyl chloride (3.12 g) at 5°-10° C. After being stirred for 1 hour at room temperature, the mixture was washed with water, dried over sodium sulfate and concentrated. To the resulting oil was added toluene (33 ml) and then 28% sodium methoxide in methanol (4.6 ml) and stirring was continued for an additional 16 hours at room temperature. The mixture was extracted with water (50 ml) and the aqueous layer was acidified to pH 2 with 6N HCl and extracted with dichloromethane. The resulting organic layer was washed with water, dried over sodium sulfate and concentrated to a viscous oil, which was submitted to silica gel column chromatography (SiO2, 100 g) and eluted with a mixed solvent (CH2Cl2 :CH3OH 4:1) to give the title product as a viscous oil.

Workup

  1. customat 5°-10° C
  2. washthe mixture was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. additionTo the resulting oil was added toluene (33 ml)
  6. stirring28% sodium methoxide in methanol (4.6 ml) and stirring
  7. waitwas continued for an additional 16 hours at room temperature
  8. extractionThe mixture was extracted with water (50 ml)
  9. extractionextracted with dichloromethane
  10. washThe resulting organic layer was washed with water
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated to a viscous oil, which
  13. washeluted with a mixed solvent (CH2Cl2 :CH3OH 4:1)

Sources & evidence

ORD record
ord-01873efe98c04c2a946255d4689ef668
Source dataset
uspto-grants-1987_09
Patent number
US04694080

Reaction notes

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