Ethyl chloroformate → [3-(3,4-Dichloro-phenyl)-3-tetrazol-2-yl-propyl]-methyl-amine

HRID 1951612Notes

Reaction equation

HRID 1951612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:15]2[N:19]=[N:18][CH:17]=[N:16]2)[CH2:10][CH2:11][N:12](C)[CH3:13])[CH:5]=[CH:6][C:7]=1[Cl:8].C(OC(Cl)=O)C.C([O-])(O)=O.[Na+].[OH-].[K+]>C(Cl)(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:15]2[N:19]=[N:18][CH:17]=[N:16]2)[CH2:10][CH2:11][NH:12][CH3:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 516892Sodium Bicarbonate2×HCID 49866033[3-(3,4-Dichloro-phenyl)-3-tetrazol-2-yl-propyl]-dimethyl-amine

Product 1

HCID 44511399[3-(3,4-Dichloro-phenyl)-3-tetrazol-2-yl-propyl]-methyl-amineYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [3-(3,4-Dichloro-phenyl)-3-tetrazol-2-yl-propyl]-dimethyl-amine (2 mmol) in chloroform was added ethylchloroformate (>10 equiv.) and NaHCO3 (>20 equiv.) and this solution was refluxed for 3 h. After that, chloroform was evaporated and ethyl acetate was added and then this organic layer was washed with water 3 times. It was dried over MgSO4, filtered, evaporated and the filtrate was concentrated at reduced pressure. The residue was dissolved in ethanol and potassium hydroxide (>20 equiv.) dissolved in water was added and refluxed for 3 days. After that, ethyl acetate and sat. NaHCO3 were added and the organic layer was extracted. It was dried over MgSO4, filtered, evaporated and the filtrate was concentrated at reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate and methanol: Yield 80%

Workup

  1. temperaturethis solution was refluxed for 3 h
  2. customAfter that, chloroform was evaporated
  3. additionethyl acetate was added
  4. washthis organic layer was washed with water 3 times
  5. dry with materialIt was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. concentrationthe filtrate was concentrated at reduced pressure
  9. dissolutionThe residue was dissolved in ethanol
  10. additionwas added
  11. temperaturerefluxed for 3 days
  12. extractionthe organic layer was extracted
  13. dry with materialIt was dried over MgSO4
  14. filtrationfiltered
  15. customevaporated
  16. concentrationthe filtrate was concentrated at reduced pressure
  17. customThe residue was purified by column chromatography
  18. washeluting with ethyl acetate and methanol

Sources & evidence

ORD record
ord-b95b39df6ccb4ba69913c0ef3b3a78e8
Source dataset
uspto-grants-2013_03
Patent number
US08404730B2

Reaction notes

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