Water → 1,1-Bis-(cyclohexyl)-5-methyl biuret

HRID 1673103Notes

Reaction equation

HRID 1673103 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[O:4].[H-].[Na+].[CH:8]1([N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:15](Cl)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.O>O1CCCC1>[CH:8]1([N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:15]([NH:5][C:3]([NH:2][CH3:1])=[O:4])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 11719MethylureaHCID 24758Sodium hydrideHCID 222909Dicyclohexylcarbamoyl chloride

Product 1

HCID 119937811,1-Bis-(cyclohexyl)-5-methyl biuretYield 0.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in General Procedure 1. To methyl urea (0.24 g) in tetrahydrofuran was added sodium hydride (22 mg of 60% in oil) and the reaction mixture stirred for 50 min at room temp. Dicyclohexyl carbamoyl chloride (0.8 g) was then added (ice bath cooling used during addition) and the mixture was stirred overnight. The reaction mixture was then added to 0.5 ml water, partially concentrated in vacuo and water (2 mL) and ethyl acetate (10 mL) was added. The non soluble material was removed by filtration and the organic layer collected and concentrated in vacuo. An aliquot of the crude was then dissolved in THF and purified by preparative LCMS to give the desired product (8 mg).

Workup

  1. customPrepared
  2. temperature(ice bath cooling used during addition)
  3. stirringthe mixture was stirred overnight
  4. concentrationpartially concentrated in vacuo and water (2 mL) and ethyl acetate (10 mL)
  5. additionwas added
  6. customThe non soluble material was removed by filtration
  7. customthe organic layer collected
  8. concentrationconcentrated in vacuo
  9. dissolutionAn aliquot of the crude was then dissolved in THF
  10. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-9bad36374dab456d809deda663541c35
Source dataset
uspto-grants-2011_08
Patent number
US07999114B2

Reaction notes

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