1,4-Dihydroxy-2-naphthoic acid → N,N'-Dicyclohexylurea

HRID 1706005Notes

Reaction equation

HRID 1706005 reaction equation
[OH:1]C1C2C(=CC=CC=2)C(O)=CC=1C(O)=O.[OH-].[Na+].BrC(CC(OCC)=O)C(OCC)=O.C(NCCCC)CCCCCCCCCCC.[CH:48]1([N:54]=[C:55]=[N:56][CH:57]2[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]2)[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1>CN(C=O)C.O1CCOCC1>[CH:57]1([NH:56][C:55](=[O:1])[NH:54][CH:48]2[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]2)[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1

Participants

8

Reactant 5

HCID 6711,4-Dihydroxy-2-naphthoic acidHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 408568N-butyl-N-dodecylamineHCID 13598458Diethyl 2-bromobutanedioate

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.05 mole of 1,4-dihydroxy-2-naphthoic acid was dissolved in 70 ml of DMF, and 10 ml of a 40% aqueous solution of sodium hydroxide was added dropwise to the solution while introducing nitrogen gas. Then, 0.05 mole of diethyl α-bromo-succinate dissolved in 15 ml of DMF was added dropwise, and the reaction was conducted at 50° C. for 3 to 4 hours under agitation. After completion of the reaction, the reaction mixture was poured into ice-hydrochloric acid, and crystals were recovered by filtration and recrystallized from acetonitrile to obtain a compound having a melting point of 176° C. Then, 0.01 mole of the so obtained compound and 0.01 mole of n-dodecylbutylamine were dissolved in 60 ml of dry dioxane, and 0.01 mole of dicyclohexylcarbodiimide was added to the solution and the reaction was carried out at 50° C. for about 30 minutes. After completion of the reaction, the reaction mixture was filtered and dicyclohexyl urea formed as a by-product was removed. The filtrate was concentrated under reduced pressure and separated by column chromatography to obtain a compound having a melting point of 68° C. (the yield being 35%). From results of the elementary analysis and the like, it was confirmed that the so obtained compound was the compound (4) illustrated above.

Workup

  1. additionwhile introducing nitrogen gas
  2. additionwas added dropwise
  3. customAfter completion of the reaction
  4. filtrationwere recovered by filtration
  5. customrecrystallized from acetonitrile
  6. customto obtain a compound
  7. waitthe reaction was carried out at 50° C. for about 30 minutes
  8. customAfter completion of the reaction
  9. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-7e6bdca110a646428f89735824fe58fe
Source dataset
uspto-grants-1980_06
Patent number
US04205990

Reaction notes

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