Dicyclohexylcarbodiimide → HCID 21976135, compound

HRID 11734Notes

Reaction equation

HRID 11734 reaction equation
[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[N:9](C1C=CC=CC=1)[C:10](=[O:14])[C:11]([OH:13])=O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:47][C:48]1[CH:53]=[C:52]([CH3:54])[CH:51]=[C:50]([C:55]([CH3:58])([CH3:57])[CH3:56])[C:49]=1[OH:59]>C1COCC1>[C:3]1([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:21])[C:2]=1[NH:9][C:10](=[O:14])[C:11]([NH:47][C:48]1[CH:53]=[C:52]([CH3:54])[CH:51]=[C:50]([C:55]([CH3:57])([CH3:56])[CH3:58])[C:49]=1[OH:59])=[O:13]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5964582-Amino-6-tert-butyl-4-methyl-phenolHCID 21976145HCID 21976145, compound

Product 1

HCID 21976135HCID 21976135, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-(Mesityl)-oxanilic acid (2.15 g, 10.4 mmol, 1.0 eq), prepared according to the synthesis method described in Example 5, and 1-hydroxybenzotriazole (2.39 g, 15.6 mmol, 1.5 eq) were added to an oven dried, two-necked flask, forming a solution. THF (100 ml) was then added and the solution was cooled to 0° C. 1,3-dicyclohexylcarbodiimide (1 M in CH2Cl2) (12.5 ml, 12.5 mmol, 1.2 eq) was then added to the solution. The solution was then allowed to stir at 0° for one hour. During this time, a white precipitate formed. 2-amino-4-methyl-6-tert-butylphenol (1.863 g, 10.4 mmol, 1.0 eq), prepared according to the synthesis method described in Example 6, was then added to the suspension. The suspension was then allowed to stir overnight. The next day, the solvent was removed under reduced pressure, and ethyl acetate was added. The resulting suspension was then filtered to remove the solid. The filtrate was washed with 10% citric acid solution (2×50 ml), 5% NaHCO3 (2×50 ml) and brine (50 ml). It was dried over MgSO4, and the solvent was removed under reduced pressure, leaving a solid which was recrystallized from hexane to give the product as a white solid (2.92 g, 7.9 mmol, 76% yield). 1H NMR (300 MHz, CDCl3) δ 9.55 (s, 1H), 8.77 (s, 1H), 7.84 (s, 1H), 7.05 (d, J=1.8 Hz, 1H), 6.92 (m, 3H), 2.30 (s, 3H), 2.28 (s, 3H), 2.22 (s, 6H), 1.45 (s, 9H); 13C NMR (75 MHz, CDCl3) δ 158.5, 157.4, 146.2, 140.6, 138.1, 134.9, 129.9, 129.6, 129.4, 126.9, 124.9, 121.4, 35.3, 30.0, 21.2, 21.0, 18.5. Anal. Calcd for C22H28N2O3: C, 71.71; H, 7.66; N, 7.60. Found: C, 72.01; H, 8.03; N, 7.36.

Workup

  1. customaccording to the synthesis method
  2. additionwere added to an oven
  3. customdried
  4. customtwo-necked flask, forming a solution
  5. customDuring this time, a white precipitate formed
  6. customaccording to the synthesis method
  7. additionwas then added to the suspension
  8. stirringto stir overnight
  9. customThe next day, the solvent was removed under reduced pressure, and ethyl acetate
  10. additionwas added
  11. filtrationThe resulting suspension was then filtered
  12. customto remove the solid
  13. washThe filtrate was washed with 10% citric acid solution (2×50 ml), 5% NaHCO3 (2×50 ml) and brine (50 ml)
  14. dry with materialIt was dried over MgSO4
  15. customthe solvent was removed under reduced pressure
  16. customleaving a solid which
  17. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-5d6f768b9327470e9be2d5fc1997a9f5
Source dataset
uspto-grants-2006_08
Patent number
US07098278B2

Reaction notes

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