Formic Acid → N,N'-Dicyclohexylurea

HRID 2396735Notes

Reaction equation

HRID 2396735 reaction equation
C(O)=[O:2].[CH:4]1([N:10]=[C:11]=[N:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:11]([NH:10][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)([NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:2]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of formic acid (0.504 mL, 13.36 mmol) in chloroform (37 mL) was added dropwise dicyclohexylcarbodiimide (DCC) (2.75 g, 13.36 mmol) in chloroform (37 mL) at 0° C. After 5 min., the above solution was added to the compound 9 (2.5 g, 6.68 mmol) in pyridine (20 mL). The mixture was then stirred for 1 hours at room temperature. Evaporation of solvent was followed by addition of ether gave dicyclohexylurea which was removed via filtration and the solid was washed with ether. The combined filtrate was concentrated and purified by flash column chromatography to give the compound 11, R1 =C5H11 (EM-401) (2.5 g, 93%) The NMR spectroscopy analysis gave a (4:1) mixture of two conformers, M.P. 149°-151° C.; 1H NMR (CDCl3): δ 0.67 (s ,3H), 0.86 (s, 3H), 0.82-1.19 (m, 6H), 1.21-1.42 (m, 11H), 1.56-1.57 (m, 2H), 1.69-1.91 (m, 4H), 1.92-1.97 (m, 3H), 2.38-2.43 (m, 2H), 2.89 (s, 3H ), 3.0 (dd, 1H, J=3.2, 12.4 Hz), 3.21-3.28 (m, 3H), 8.14 (s, 0.8H), 8.2 (s, 0.2H); 13C NMR (CDCl3):δ 170 .56, 164.8, 162.97, 68.54, 65.58, 61.98, 51.93, 51.66, 51.24, 46.69, 44.28, 37.24, 36.8, 36.37, 34.07, 32.83, 32.12, 29.64, 29.13, 29.04, 28.8, 28.19, 25.15, 24.33, 23.22, 22.84, 22.36, 20.51, 13.94, 12.75, 12.32;HRMS: calcd for C25H42O2N2, 402.3245, found 402.3242.

Workup

  1. customEvaporation of solvent
  2. additionwas followed by addition of ether

Sources & evidence

ORD record
ord-ad61ca636f194d22b3f0807222019402
Source dataset
uspto-grants-1996_02
Patent number
US05494914

Reaction notes

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