Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 2425727Notes

Reaction equation

HRID 2425727 reaction equation
C[O:2]C1C=CC(C=CC(O)=O)=CC=1.[CH:14]1([N:20]=[C:21]=[N:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.NCCC[Si](OC)(OC)OC>>[CH:23]1([NH:22][C:21]([NH:20][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[O:2])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 132454-Methoxy cinnamic acidHCID 83756Aminopropyltrimethoxysilane

Product 1

HCID 4277N,N'-Dicyclohexylurea

Procedure

30 g of p-methoxycinnamic acid and 35.1 g of dicyclohexylcarbodiimide were added to a 1 L round 3-necked flask equipped with a dropping funnel and a cooler, 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, 37.5 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 (TLC). Yield of the resultant product is about 40 g.

Workup

  1. customequipped with a dropping funnel
  2. distillationa cooler, 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-17fa5c0950cd4abbb126656f812e2527
Source dataset
uspto-grants-2011_06
Patent number
US07964747B2

Reaction notes

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