Tetrahydrofuran → N,N'-Dicyclohexylurea

HRID 892406Notes

Reaction equation

HRID 892406 reaction equation
[CH:1]1([N:7]=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C[O:19]CC1>CC#N>[C:8]([NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:19]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-DicyclohexylureaYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

O,O-Dibenzoyl tartaric acid monohydrate (18.8 g, 50 mmole) was dissolved in 250 ml CH3CN and the solvent was removed in vacuo. This process was repeated. The resulting oil was dissolved in 250 ml THF and dicyclohexylcarbodiimide (DCC) (10.6 g, 50 mmole) dissolved in 50 ml THF was added. A precipitate started forming in a few minutes. After stirring for 18 hr at 20° C. the reaction mixture was filtered, and the precipitate washed with a little THF. The precipitate was then dried in high vacuum to give 10.8 g (100%, 50 mmole) dicyclohexylurea (DCHU). To the combined filtrate was added 2-(N-methyl)aminoethanol (4.0 ml, 50 mmole) and the reaction mixture was stirred for 1 hr at 20° C. Then, DCC (10.6 g, 50 mmole) in 50 ml THF was added; a small precipitate was formed. After about 1 hr, 2-(N-methyl)aminoethanol (4.0 ml, 50 mmole) was added and the reaction mixture stirred for 18 hours at 20° C.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe resulting oil was dissolved in 250 ml THF
  3. additionwas added
  4. customA precipitate started forming in a few minutes
  5. filtrationwas filtered
  6. washthe precipitate washed with a little THF
  7. customThe precipitate was then dried in high vacuum

Sources & evidence

ORD record
ord-cbdf48d2da2b45bd89e09ac8172a9fd1
Source dataset
uspto-grants-1992_06
Patent number
US05118605

Reaction notes

Loading…