Triethylamine → HCID 19979375, compound

HRID 1461770Notes

Reaction equation

HRID 1461770 reaction equation
[C:1]([NH:5][C:6]([NH:8][C:9]1[C:10]([CH:26]([CH3:28])[CH3:27])=[N:11][C:12]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:13][C:14]=1[CH:15]([CH3:17])[CH3:16])=S)([CH3:4])([CH3:3])[CH3:2].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>C(#N)C>[C:1]([N:5]=[C:6]=[N:8][C:9]1[C:10]([CH:26]([CH3:28])[CH3:27])=[N:11][C:12]([O:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[CH:13][C:14]=1[CH:15]([CH3:17])[CH3:16])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 19979380HCID 19979380, compound

Product 1

HCID 19979375HCID 19979375, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3.0 g of 1-tert.-butyl-3-[2,4-diisopropyl-6-(4-chlorophenoxy)-pyrid-3-yl]-thiourea and 2.1 g of 2-chloro-1-methylpyridinium iodide are placed in 20 ml of acetonitrile and, at room temperature, a solution of 1.6 g of triethylamine in 7 ml of acetonitrile is added. The reaction mixture is then stirred for 1 hour at approximately +65° C. After evaporation of the solvent, the residue is taken up in hexane/water. The organic phase is dried over magnesium sulfate and the solvent is removed in vacuo. The crude product is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:5). 1-tert.-Butyl-3-[2,4-diisopropyl-6-(4-chlorophenoxy)-pyrid-3-yl]-carbodiimide is obtained in the form of a colourless oil which solidifies after a few hours. M.p. 46°-55° C.

Workup

  1. customAfter evaporation of the solvent
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed in vacuo
  4. customThe crude product is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:5)

Sources & evidence

ORD record
ord-f132bb0566cc4a2f874afcbacd2974b1
Source dataset
uspto-grants-1991_12
Patent number
US05077304

Reaction notes

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