Imidazole → HCID 86752535, compound

HRID 1289458Notes

Reaction equation

HRID 1289458 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7](Cl)=[CH:6][C:5]=1[NH:15][CH:16]([P:18]([OH:21])(=[O:20])[OH:19])[CH3:17])([O-:3])=[O:2].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.[CH2:27](OC(OCC)OCC)[CH3:28].[C:37]1(C)C=CC(S(O)(=O)=O)=C[CH:38]=1>O>[CH2:27]([O:19][P:18]([CH:16]([NH:15][C:5]1[CH:6]=[C:7]([C:23]2[NH:22][CH:26]=[CH:25][N:24]=2)[C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:17])(=[O:20])[O:21][CH2:37][CH3:38])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 21847743HCID 21847743, compound

Product 1

HCID 86752535HCID 86752535, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.67 g (5 mmol) of 1-[(2-nitro-4-trifluoromethyl-5-chloro-phenyl)amino]ethanephosphonic acid (according to example 8, A) is stirred together with 1.70 g of imidazole for 4 hours at 160° C. bath temperature. It is taken up in 100 ml of water and stirred twice with ion exchanger IR 120 (strong acid form, Amberlite, 20-50 mesh) and suctioned off. Then, it is evaporated to dryness in a rotary evaporator and the residue is heated with 24 ml of orthoformic acid triethyl ester and 156 mg (0.82 mmol) of p-toluene sulfonic acid for 10 hours to 150° C. bath temperature. After evaporation to dryness in a rotary evaporator, it is chromatographed on silica gel with methylene chloride:ethanol=10:1. 222 mg (17% of theory) of 1-[(2-nitro-4-trifluoromethyl-5-imidazolylphenyl)amino]ethanephosphonic acid diethyl ester is obtained.

Workup

  1. customThen, it is evaporated to dryness in a rotary evaporator
  2. customAfter evaporation to dryness
  3. customin a rotary evaporator, it
  4. customis chromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-a906099faac84f3b934307aecb32dbe3
Source dataset
uspto-grants-1998_05
Patent number
US05750525

Reaction notes

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