Dicyclohexylcarbodiimide → HCID 57852678, compound

HRID 657465Notes

Reaction equation

HRID 657465 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])=[O:24]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 119232-Nitrobenzyl alcoholHCID 1781211-Bromoundecanoic acid

Product 1

HCID 57852678HCID 57852678, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

One equivalent of 2-nitrobenzyl alcohol (1.91 g, 12.49 mmol) was combined with one equivalent of 11-bromoundecanoic acid (3.31 g, 12.49 mmol), 0.1 equivalents DMAP (0.153 g, 1.25 mmol) and dissolved in 100 mL CH2Cl2. To this mixture a solution of DCC (2.58 g, 12.49 mmol) in 50 mL CH2Cl2 was slowly added while stirring. Upon addition a yellow-brown precipitate formed after a few minutes. The mixture was stirred at room temperature overnight. The precipitate was removed by vacuum filtration and the solvent was removed by rotovap. The product was purified using silica gel column chromatography with CH2Cl2/MeOH (v/v 50:1) as eluent. The product was dried over Na2SO4, the solvent removed by rotovap, and dried under vacuum, producing a white solid. Yield: 4.37 g (87.4%). 1H-NMR (CDCl3) δ (ppm): 8.1 (d, 1H, Ar), 7.6 (t, 1H, Ar), 7.5 (d, 1H, Ar), 7.4 (t, 1H, Ar), 5.5 (s, 2H, O—CH2), 3.4 (t, 2H, CH2—Br), 2.4 (t, 2H, CH2—C═O), 1.8 (m, 2H, CH2), 1.6 (m, 2H, CH2), 1.4 (m, 2H, CH2), 1.3 (m, 10H, CH2). 13C-NMR (CDCl3) δ (ppm): 173.5, 147.9, 134.1, 132.7, 129.5, 129.2, 125.5, 63.2, 34.6, 34.5, 33.2, 29.7, 29.6, 29.5, 29.4, 29.1, 28.5, 25.3.

Workup

  1. additionUpon addition a yellow-brown precipitate
  2. customformed after a few minutes
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThe precipitate was removed by vacuum filtration
  5. customthe solvent was removed by rotovap
  6. customThe product was purified
  7. dry with materialThe product was dried over Na2SO4
  8. customthe solvent removed by rotovap
  9. customdried under vacuum
  10. customproducing a white solid

Sources & evidence

ORD record
ord-006fc63dc383414592907d6e0b9339b4
Source dataset
uspto-grants-2011_12
Patent number
US08076125B2

Reaction notes

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