Ethyl Bromide → HCID 23465188, compound

HRID 443727Notes

Reaction equation

HRID 443727 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:10]2)=[CH:5][CH:4]=1.C(Br)C.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26]>>[CH2:25]([O:24][P:23]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:10]2)=[CH:5][CH:4]=1)([O:27][CH2:28][CH3:29])=[O:30])[CH3:26]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 31215Triethyl phosphiteHCID 23465185HCID 23465185, compound

Product 1

HCID 23465188HCID 23465188, compound

Procedure

155.6 g of 2-(p-bromomethyl-phenyl)-4-methyl-5-carboethoxy-2H-1,2,3-triazole in 430 ml of triethyl phosphite are heated to 150° C. in the course of 21/2 hours and the mixture is kept at this temperature for 3 hours, with stirring, ethyl bromide distilling off. The reaction mixture is evaporated under a waterpump vacuum. The residual dark viscous oil is dissolved in 300 ml of methylene chloride and, after the addition of bleaching earth, the solution is filtered to give a clear filtrate and 300 ml of hexane are added to the filtrate. The resulting mixture is then concentrated to 200 ml and cooled to 0° to 5° C. and the product which has crystallised out is filtered off with suction and dried in vacuo. This gives 56.6 g of 2-(p-diethylphosphonomethyl-phenyl)-4-methyl-5-carboethoxy-2H-1,2,3-triazole of the formula ##STR59##

Workup

  1. customThe reaction mixture is evaporated under a waterpump vacuum
  2. dissolutionThe residual dark viscous oil is dissolved in 300 ml of methylene chloride
  3. additionafter the addition
  4. filtrationthe solution is filtered
  5. customto give a clear filtrate and 300 ml of hexane
  6. additionare added to the filtrate
  7. concentrationThe resulting mixture is then concentrated to 200 ml
  8. temperaturecooled to 0° to 5° C.
  9. customthe product which has crystallised out
  10. filtrationis filtered off with suction
  11. customdried in vacuo

Sources & evidence

ORD record
ord-3e5325530b584e88ac5af723a76723ad
Source dataset
uspto-grants-1981_04
Patent number
US04261855

Reaction notes

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