Triethylamine → HCID 19888654, compound

HRID 654140Notes

Reaction equation

HRID 654140 reaction equation
[C:1]([NH:5][C:6]([NH:8][C:9]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][S:11][C:10]=1[CH:17]([CH3:19])[CH3:18])=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:13]([CH:14]([CH3:15])[CH3:16])=[CH:12][S:11][C:10]=1[CH:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 19888651HCID 19888651, compound

Product 1

HCID 19888654HCID 19888654, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2.50 g of the 1-tert.-butyl-3-(2,4-diisopropyl-3-thienyl)thiourea obtained according to Example 2 and 2.60 g of 2-chloro-1-methylpyridinium iodide are introduced into 25 ml of acetonitrile and, at room temperature, a solution of 1.90 g of triethylamine in 12 ml of acetonitrile is added. The reaction mixture is then stirred for 2 hours at approximately +45° C. After evaporation of the solvent, the residue is taken up in hexane/water. The separated 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-1:20). The title compound of formula ##STR13## is obtained in the form of a colourless oil, nD23 =1.5249 (compound No. 4.01).

Workup

  1. customAfter evaporation of the solvent
  2. dry with materialThe separated 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-1:20)

Sources & evidence

ORD record
ord-58f8bbf3be394f39acba290603397a8b
Source dataset
uspto-grants-1992_07
Patent number
US05130331

Reaction notes

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