Reaction #619108

Reaction equation

1,1-dicyclohexyl-3-(4-hydroxymethyl-thiazol-2-yl)urea

pyridine-sulfur trioxide

triethyl-amine

→

1,1-dicyclohexyl-3-(4-formyl-thiazol-2-yl)urea

Yield 95.2%

Solvents

DCM DMSO

Conditions

Workup

1. 1
   Otherquenched with water (50 mL)
2. 2
   Otherthe layers were separated
3. 3
   ExtractionThe aqueous layer was extracted with DCM (2×50 mL)
4. 4
   WashThe combined organic layers was washed with water, saturated ammonium chloride solution, brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   Concentrationconcentrated in vacuo

Procedure

To a solution of 1,1-dicyclohexyl-3-(4-hydroxymethyl-thiazol-2-yl)urea (850 mg, 2.5 mmol) in 4:1 DCM/DMSO (8 mL) was added pyridine-sulfur trioxide (1.59 g, 10.0 mmol) and triethyl-amine (1.55 mL, 11.25 mmol) at 0° C. The mixture was stirred for 6 h and quenched with water (50 mL) and the layers were separated. The aqueous layer was extracted with DCM (2×50 mL). The combined organic layers was washed with water, saturated ammonium chloride solution, brine, dried over sodium sulfate and concentrated in vacuo to obtain 1,1-dicyclohexyl-3-(4-formyl-thiazol-2-yl)urea (800 mg, 2.38 mmol).

Source