2-Propenoic acid, 3-phenyl- → N,N'-Dicyclohexylurea

HRID 2425728Notes

Reaction equation

HRID 2425728 reaction equation
C(O)(=[O:10])C=CC1C=CC=CC=1.[CH:12]1([N:18]=[C:19]=[N:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.NCCC[Si](OC)(OC)OC>>[CH:21]1([NH:20][C:19]([NH:18][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[O:10])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 87842-Propenoic acid, 3-phenyl-HCID 10868DicyclohexylcarbodiimideHCID 83756Aminopropyltrimethoxysilane

Product 1

HCID 4277N,N'-Dicyclohexylurea

Procedure

40 g of cinnamic acid and 50 g of dicyclohexylcarbodiimide were added to a 1 L round 3-necked flask equipped with a dropping funnel and a cooler, and also 600 mL of toluene newly distilled from sodium ketyl was added thereto, and the resultant mixture was refluxed to yield a homogeneous solution. After about 30 minutes, 48 g of 3-aminopropyltrimethoxysilane was dropped over 30 minutes through the dropping funnel. The resultant reaction mixture was refluxed for 4 hours, and then toluene was removed by vacuum distillation without contacting with moisture. Dicyclohexyl urea formed in a remaining solution was removed by filtration to yield a product. The resultant product was determined using FT-IR and thin layer chromatography. Yield of the resultant product is about 30 g.

Workup

  1. customequipped with a dropping funnel
  2. distillationa cooler, and also 600 mL of toluene newly distilled from sodium ketyl
  3. additionwas added
  4. temperaturethe resultant mixture was refluxed
  5. customto yield a homogeneous solution
  6. customThe resultant reaction mixture
  7. temperaturewas refluxed for 4 hours
  8. customtoluene was removed by vacuum distillation

Sources & evidence

ORD record
ord-350a72d192f7414c9c2a8111454f651c
Source dataset
uspto-grants-2011_06
Patent number
US07964747B2

Reaction notes

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