Triethylamine → 1,1-Dicyclohexyl-3-(4-formyl-thiazol-2-yl)urea

HRID 253793Notes

Reaction equation

HRID 253793 reaction equation
[CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CN=CC=1.O=S(=O)=O.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[CH:18]1([N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([CH:16]=[O:17])[N:15]=2)=[O:9])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 578836131,1-Dicyclohexyl-3-(4-hydroxymethyl-thiazol-2-yl)urea

Product 1

HCID 578836681,1-Dicyclohexyl-3-(4-formyl-thiazol-2-yl)ureaYield 95.2%

Reagents, catalysts & solvents 1

HCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

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).

Workup

  1. customquenched with water (50 mL)
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  4. washThe combined organic layers was washed with water, saturated ammonium chloride solution, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2357be24d23442f9f877f7886627c92
Source dataset
uspto-grants-2011_01
Patent number
US07872139B2

Reaction notes

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