2-Chloroethyl methyl ether → HCID 14991003, compound

HRID 2248345Notes

Reaction equation

HRID 2248345 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[N:13][N:12]([OH:15])[C:11]=3[CH:16]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[H][H].Cl[CH2:22][CH2:23][O:24][CH3:25].COCCOCCN(CCOCCOC)CCOCCOC>O.CS(C)=O.CN(C)C=O>[N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[N:13][N:12]([O:15][CH2:22][CH2:23][O:24][CH3:25])[C:11]=3[CH:16]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

9

Reactant 5

HCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 14990941HCID 14990941, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14991003HCID 14991003, compoundYield 46.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred and heated (50° C.) mixture of 2.81 parts of 6-(1H-imidazol-1-ylmethyl)-1H-benzotriazol-1-ol and 22.5 parts of N,N-dimethylformamide were added 0.69 parts of a sodium hydride dispersion. The reaction mixture was stirred until hydrogen evolution had ceased. 1.28 Parts of 1-chloro-2-methoxyethane were added at room temperature and stirring was continued for a while. 22 Parts of dimethyl sulfoxide and 0.04 parts of 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]ethanamine were added. The reaction mixture was stirred overnight at 50° C. and then poured into water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of ethyl acetate and 2,2'-oxybispropane (1:3 by volume). The product was filtered off, washed with a mixture of ethyl acetate and 2,2'-oxybispropane (1:3 by volume) and 2,2'-oxybispropane and dried in vacuo at 50° C., yielding 1.66 parts (46.7%) of 6-(1H-imidazol-1-ylmethyl)-1-(2-methoxyethoxy)-1H-benzotriazole; mp. 77.0° C. (compound 220).

Workup

  1. temperatureheated
  2. stirringstirring
  3. stirringThe reaction mixture was stirred overnight at 50° C.
  4. extractionThe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from a mixture of ethyl acetate and 2,2'-oxybispropane (1:3 by volume)
  13. filtrationThe product was filtered off
  14. washwashed with a mixture of ethyl acetate and 2,2'-oxybispropane (1:3 by volume) and 2,2'-oxybispropane
  15. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-475f0cb553514d9084957fbf14ff47d9
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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