Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → HCID 14990577, compound

HRID 2166037Notes

Reaction equation

HRID 2166037 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].COCCOCCN(CCOCCOC)CCOCCOC.[CH3:29][N:30]1[C:34]2[C:35]([CH2:39][OH:40])=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[N:31]1>ClCCl>[CH3:29][N:30]1[C:34]2[C:35]([CH:39]=[O:40])=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[N:31]1

Participants

5

Reactant 3

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 516875Potassium PermanganateHCID 14990571HCID 14990571, compound

Product 1

HCID 14990577HCID 14990577, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 7.4 parts of potassium permanganate, 0.6 parts of 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]ethanamine and 130 parts of dichloromethane was added dropwise a solution of 7.6 parts of 1-methyl-1H-benzotriazole-7-methanol in dichloromethane. Upon complete addition, stirring was continued for 2 hours. The reaction mixture was filtered over diatomaceous earth and washed with dichloromethane. The organic layer was washed with 30 parts of a hydrochloric acid solution 2N and then with a sodium carbonate solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 3.5 parts (46.6%) of 1-methyl-1H-benzotriazole-7-carboxaldehyde; mp. 126° C. (int. 18).

Workup

  1. additionUpon complete addition
  2. filtrationThe reaction mixture was filtered over diatomaceous earth
  3. washwashed with dichloromethane
  4. washThe organic layer was washed with 30 parts of a hydrochloric acid solution 2N
  5. dry with materialwith a sodium carbonate solution, dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-00093a258af5406a9ba49be5ee82d016
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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