Phosphorus pentachloride → 1-(3,5-bis-trifluoromethyl-benzyl)-5-chloro-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 349251Notes

Reaction equation

HRID 349251 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH2:7]([O:9][C:10]([C:12]1[N:13]=[N:14][N:15]([CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[C:16]=1O)=[O:11])[CH3:8]>C1(C)C=CC=CC=1>[CH2:7]([O:9][C:10]([C:12]1[N:13]=[N:14][N:15]([CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[C:16]=1[Cl:2])=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178470506HCID 178470506, compound

Product 1

HCID 866012051-(3,5-bis-trifluoromethyl-benzyl)-5-chloro-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combine PCl5 (5.73 g, 27.5 mmol) with a solution of 1-(3,5-bis-trifluoromethyl-benzyl)-5-hydroxy-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (5.30 g, 13.8 mmol) in toluene (150 mL) and heat to 50° C. After 2 h, cool to RT, concentrate solution and dissolve crude material in ether (100 mL). Wash the organic solution with saturated NaHCO3 (2×100 mL) and brine (100 mL), dry, filter, and concentrate. Purify the crude material by passing through a short plug of silica gel using a linear gradient of 50% to 80% EtOAc/hexanes, then recrystallize from 1:1 diethyl ether:petroleum ether (150 mL). MS (ES) 402.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.76 (s, 2H), 5.67 (s, 2H), 4.43 (q, 2H, J=7.0 Hz), 1.40 (t, 3H, J=7.0 Hz).

Workup

  1. concentrationconcentrate solution
  2. dissolutiondissolve crude material in ether (100 mL)
  3. washWash the organic solution with saturated NaHCO3 (2×100 mL) and brine (100 mL)
  4. customdry
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material
  8. customrecrystallize from 1:1 diethyl ether

Sources & evidence

ORD record
ord-01f7440dd6c04e7ba79e582e44ad1e90
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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