Dicyclohexylcarbodiimide → HCID 19882813, compound

HRID 846511Notes

Reaction equation

HRID 846511 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][CH3:18])[N:12]=[N:11]1.[CH2:19](O)[C:20]#[C:21][CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:19][C:20]#[C:21][CH3:22])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][CH3:18])[N:12]=[N:11]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 129912-Butyn-1-olHCID 19882809HCID 19882809, compound

Product 1

HCID 19882813HCID 19882813, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 0.5 g (0.0017 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one (Example 10, Step A) and 0.15 g (0.0021 mole) of 2-butyn-1-ol in 5 mL of acetonitrile was added 0.33 g (0.0016 mole) of dicyclohexylcarbodiimide. The reaction mixture was heated at reflux temperature for 4 days, cooled to room temperature, and filtered. The filtrate was washed with 10 mL of a 10% aqueous sodium hydroxide solution, diluted with methylene chloride, and washed with 10 mL of 6N hydrochloric acid. The washed organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated to leave an oil. The oil was purified by column chromatography on silica gel, eluting with ethyl acetate: heptane (20:80), to yield 0.12 g of 1-[2,4-dichloro-5-(2-butynyloxy)phenyl]-1,4-dihydro-4-propyl-5H-tetrazol-5-one as a solid, mp 58°-60° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 4 days
  3. filtrationfiltered
  4. washThe filtrate was washed with 10 mL of a 10% aqueous sodium hydroxide solution
  5. additiondiluted with methylene chloride
  6. washwashed with 10 mL of 6N hydrochloric acid
  7. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated
  10. customto leave an oil
  11. customThe oil was purified by column chromatography on silica gel
  12. washeluting with ethyl acetate: heptane (20:80)

Sources & evidence

ORD record
ord-f1aec66fef634e2e88c8e4b96bd86973
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

Loading…