Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1489826Notes

Reaction equation

HRID 1489826 reaction equation
C(CCSSC1C=CC=CN=1)(O)=[O:2].[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>C1COCC1>[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 2

HCID 10868DicyclohexylcarbodiimideHCID 118060883-[(Pyridin-2-yl)disulfanyl]propanoic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-(2-propenylhydrazone)nicotinamido-3-propanol (190 mg, 0.8 mmol) and 2-carboxyethyl-2-pyridyldisulphide (163 mg, 1.0 equiv) in THF (10 ml) at 0° C. was added dicyclohexyl-carbodiimide (157 mg, 1.0 equiv) and the mixture was stirred at 0°-5° C. for 72 hours during which time a white solid precipitated. The white solid was filtered off and the filtrate evaporated under reduced pressure. The residue was dissolved in ethyl acetate and cooled, which gave a further precipitate of dicyclohexyl urea ("DCU"). This procedure was repeated once again until all of the urea had been removed. The desired product was purified by column chromatography on silica gel using 5% methanol in dichloromethane as eluent. Re-crystallisation in ethyl acetate/ether gave white solid (85 mg, 25%). 1H NMR (CDCl3) δ1.15 (t, 3H, J=7.5 Hz), 1.95 (pentet, 2H, J=6.0 Hz), 2.36 (dq, 2H, J=5.0, 7.6 Hz), 2.80 (t, 2H, J=7.0 Hz), 3.07 (t, 2H, J=7.0 Hz), 3.50 (m, 2H), 4.04 (t, 2H, J=6.0 Hz), 6.51 (broad triplet, 1H, D2O exchangeable), 7.07-7.12 (m, 1H, 7.17-7.21 (m, 2H), 7.60-7.72 (m, 2H), 7.95-7.99 (dd, 1H, J=8.8, 2.4 Hz), 8.22 (broad s, 1H, D2O exchangeable), 8.42-8.45 (m, 1H), 8.55 (d, 1H, J{32 2.4 Hz); mass spectrum (FAB); m/e relative intensity); 448 (100, M+1), 176 (45).

Workup

  1. customprecipitated
  2. filtrationThe white solid was filtered off
  3. customthe filtrate evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. temperaturecooled

Sources & evidence

ORD record
ord-01046c2f2c884cba88baa54e0bd4b3ed
Source dataset
uspto-grants-1997_10
Patent number
US05679778

Reaction notes

Loading…