Dimethylformamide → HCID 20489616, compound

HRID 1995067Notes

Reaction equation

HRID 1995067 reaction equation
[K].[NH:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[C:7]([C:11]1(CBr)[O:15][C:14]([CH3:25])([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH2:13][O:12]1)([CH3:10])([CH3:9])[CH3:8].[CH3:28]N(C)C=O>>[C:7]([C:11]1([N:2]2[CH:6]=[N:5][CH:4]=[N:3]2)[O:15][C:14]([CH3:25])([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH:13]([CH3:28])[O:12]1)([CH3:8])([CH3:9])[CH3:10]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 20489617HCID 20489617, compoundHCID 534465811,2,4-Triazole potassium

Product 1

HCID 20489616HCID 20489616, compound

Procedure

3.5 g of 1,2,4-triazole potassium salt in 100 ml of absolute dimethylformamide are heated to 100°. To the hot solution are added dropwise 9 g of 2-tert-butyl-2-bromomethyl-4-(2,4-dichlorophenoxy)-methyl-1,3-dioxolane dissolved in 50 ml of absolute dimethylformamide. The reaction mixture is subsequently stirred for 24 hours at 130°; the solvent is then removed in vacuo and the residue is extracted with diethyl ether; the ether phase is washed with water and dried over sodium sulfate. The yield after concentration by evaporation is 7 g of a viscous oil which, after the addition of n-hexane, crystallises to give the cis isomer, m.p. 113°-114°. The trans isomer, m.p. 73°-74°, can be obtained from the mother liquor.

Workup

  1. customthe solvent is then removed in vacuo
  2. extractionthe residue is extracted with diethyl ether
  3. washthe ether phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe yield
  6. concentrationafter concentration
  7. customby evaporation
  8. additionafter the addition of n-hexane
  9. customcrystallises
  10. customto give the cis isomer, m.p. 113°-114°
  11. customThe trans isomer, m.p. 73°-74°, can be obtained from the mother liquor

Sources & evidence

ORD record
ord-908baca882254dbc8b7bfd8e2dff1c28
Source dataset
uspto-grants-1983_09
Patent number
US04402963

Reaction notes

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