Reacción #1755463

ord-c12c168af64f4407889e699540100e3f

Ecuación de reacción

Cc1cc(C)cc(CC(NC(=S)NCCO)c2cccs2)c1
1-[2-(3,5-dimethyl-phenyl)-1-thiophen-2-yl-ethyl]-3-(2-hydroxy-ethyl)-thiourea
Cc1cc(C)cc(CC(NC(=S)NCCO)c2cccs2)c1
1-[2-(3,5-Dimethyl-phenyl)-1-thien-2-yl-ethyl]-3-(2-hydroxy-ethyl)-thiourea
CCN(C(C)C)C(C)C
diisopropyethylamine
C[P+](C)(C)CC#N.[I-]
cyanomethyl-trimethyl-phosphonium iodide
Cc1cc(C)cc(CC(NC2=NCCS2)c2cccs2)c1
title compound
Rendimiento 95.0%
Cc1cc(C)cc(CC(NC2=NCCS2)c2cccs2)c1
(4,5-Dihydro-thiazol-2-yl)-[2-(3,5-dimethyl-phenyl)-1-thien-2-yl-ethyl]-amine
Rendimiento 95.0%

Disolventes

Condiciones de reacción

Temperatura
90°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ExtracciónExtraction with ethyl acetate
  2. 2
    Lavadowashing with potassium carbonate solution and water
  3. 3
    Otroby drying
  4. 4
    Otroevaporation of the solvent

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07989394B2uspto-grants-2011_08