Diisopropylethylamine → HCID 24946389, compound

HRID 1668281Notes

Reaction equation

HRID 1668281 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:16][C:17]([NH:19][CH2:20][CH2:21]O)=[S:18])[C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(C(C)C)CC)(C)C.[I-].C(C[P+](C)(C)C)#N>C(#N)CC>[S:18]1[CH2:21][CH2:20][N:19]=[C:17]1[NH:16][CH:10]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH2:9][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 24946390HCID 24946390, compound

Product 1

HCID 24946389HCID 24946389, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[2-(3,5-dimethyl-phenyl)-1-thiophen-2-yl-ethyl]-3-(2-hydroxy-ethyl)-thiourea (0.30 g) from example 6 and diisopropyethylamine (0.16 g) in propionitrile (10 ml) was added cyanomethyl-trimethyl-phosphonium iodide (0.27 g, prepared according to Tetrahedron 2001, 57, 5451-54). The reaction mixture was heated up to 90° C. for 72 h. Extraction with ethyl acetate, washing with potassium carbonate solution and water followed by drying and evaporation of the solvent yielded 0.27 mg (95%) of the title compound as brownish oil.

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with potassium carbonate solution and water
  3. customby drying
  4. customevaporation of the solvent

Sources & evidence

ORD record
ord-c12c168af64f4407889e699540100e3f
Source dataset
uspto-grants-2011_08
Patent number
US07989394B2

Reaction notes

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