2-Aminothiazole → N,N-Dicyclopentyl-N'-1,3-thiazol-2-ylurea

HRID 731401Notes

Reaction equation

HRID 731401 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].CN(C1C=CC=CN=1)C.[CH:28]1([NH:33][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[CH2:32][CH2:31][CH2:30][CH2:29]1>ClCCl.C(OCC)(=O)C>[CH:34]1([N:33]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[C:7]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[O:8])[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 218852-DimethylaminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 247671Dicyclopentylamine

Product 1

HCID 57688319N,N-Dicyclopentyl-N'-1,3-thiazol-2-ylurea

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-aminothiazole (50 mg, 0.5 mmol) in dichloromethane was added carbonyldiimidazole (81 mg, 0.5 mmol) and dimethylaminopyridine (3 mg) and the solution stirred 1 h at room temperature. Dicyclopentylamine (77 mg) was then added and the reaction stirred overnight at room temperature. The reaction mixture is then diluted with ethyl acetate (8 mL), washed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL), dried over magnesium sulphate, concentrated in vacuo, and the residue purified by flash chlomatography (eluant 7 ethyl acetate:3 heptane)

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. washwashed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by flash chlomatography (eluant 7 ethyl acetate:3 heptane)

Sources & evidence

ORD record
ord-a25127cea0ca4f5ab6f9881ba3e33f5d
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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