Triethylamine → HCID 86751284, compound

HRID 963628Notes

Reaction equation

HRID 963628 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[C:13]([N:15]=[C:16]=[O:17])[CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].Cl.[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[CH3:27].C(N(CC)CC)C>C(Cl)Cl>[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH:31][C:16](=[O:17])[NH:15][C:13]1[CH:14]=[C:9]([O:8][C:6]2[CH:5]=[CH:4][C:3]([C:21]([F:22])([F:23])[F:24])=[C:2]([Cl:1])[CH:7]=2)[CH:10]=[CH:11][C:12]=1[N+:18]([O-:20])=[O:19])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 86751285HCID 86751285, compound

Product 1

HCID 86751284HCID 86751284, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 5-[(2-chloro-α,α,α-trifluoro-p-tolyl)oxy]-2-nitrophenyl isocyanate (107 g, 0.299) mol) in methylene chloride is cooled to 0° C., treated with a mixture of glycine ethyl ester hydrochloride (50.1 g, 0.359 mol) and triethylamine (166 mL, 1.20 mol) in methylene chloride over 10 minutes, refluxed overnight, cooled to room temperature, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. A solution of the solid in methylene chloride is placed on a silica gel plug, eluted with methylene chloride and concentrated in vacuo to give the title product as a yellow solid which is identified by 1H and 13CNMR spectral analyses.

Workup

  1. temperaturerefluxed overnight
  2. washwashed sequentially with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a solid
  6. washeluted with methylene chloride
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85d4f3168c1943e3904daab503ea2d1f
Source dataset
uspto-grants-1998_06
Patent number
US05763605

Reaction notes

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