Dimethylformamide → 1-(1-Phenyltetrazol-5-yloxy)-2,3-epoxypropane

HRID 1414020Notes

Reaction equation

HRID 1414020 reaction equation
[H-].[Na+].CN(C=O)C.[C:8]1([N:14]2[C:18](Cl)=[N:17][N:16]=[N:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:20]1[O:22][CH:21]1[CH2:23][OH:24]>CCCCCC>[O:22]1[CH2:20][CH:21]1[CH2:23][O:24][C:18]1[N:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:15]=[N:16][N:17]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 11164GlycidolHCID 24758Sodium hydrideHCID 842621H-Tetrazole, 5-chloro-1-phenyl-

Product 1

HCID 123998231-(1-Phenyltetrazol-5-yloxy)-2,3-epoxypropane

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Sodium hydride (11.9 g., 0.050 mole), washed free of mineral oil with hexane, was stirred in 1.8 l. of DMF at ice-water temperature while a solution of 72.3 g (0.40 mole) of 1-phenyl-5-chlorotetrazole and 29.6 g. (0.04 mole) of glycidol in 1.8 l. of DMF was added dropwise during 4 hours. The solution was allowed to stand at 25° overnight (16 hours), diluted with 12 l. of H2O and extracted with ethyl acetate. The extracts were washed with water, dried (Na2SO4), and evaporated to give 75.7 g. of product, m.p. 77°-81°. Recrystallization from MeOH-i-PrOH gave 55.8 g., m.p. 83°-84°.

Workup

  1. addition(16 hours), diluted with 12 l
  2. extractionof H2O and extracted with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give 75.7 g
  7. customRecrystallization from MeOH-i-PrOH
  8. customgave 55.8 g

Sources & evidence

ORD record
ord-de7d0f7308d24e54b2ab6bd020617249
Source dataset
uspto-grants-1981_02
Patent number
US04252815

Reaction notes

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