Dicyclohexylcarbodiimide → HCID 178439985, compound

HRID 1918240Notes

Reaction equation

HRID 1918240 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.O[C:17]([C:20]1[N:21]=[C:22]([CH2:28][CH2:29][CH3:30])[NH:23][C:24]=1[C:25](O)=[O:26])([CH3:19])[CH3:18]>CC(C)=O>[CH3:18][C:17]1([CH3:19])[C:20]2[NH:21][C:22]([CH2:28][CH2:29][CH3:30])=[N:23][C:24]=2[CH2:25][O:26]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 178440085HCID 178440085, compound2×

Product 1

HCID 178439985HCID 178439985, compoundYield 138.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

33.0 grams of dicyclohexylcarbodiimide (DCC) was added into a suspension of 30.0 grams of 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylic acid (formula III) in 300 ml of acetone. The reaction was performed at ambient temperature for 48 hours. The mixture was suction filtered and washed. The filtrate was concentrated and acetone was recovered. 120 ml of ethyl acetate and 120 ml of water were added into the residual liquid, and pH was adjusted to 2-3 with concentrated hydrochloric acid. The aqueous layer was separated and the organic layer was further extracted with 20 ml×2 of water. 150 ml of ethyl acetate was added into the combined aqueous portion and pH was adjusted to 10 with 30% sodium hydroxide solution. Salt was added to be saturated and the organic layer was separated. The aqueous layer was further extracted with 30 ml×2 of ethyl acetate. Combined organic portion was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated to give 35.3 grams of 4,4-dimethyl-2-propyl-4,6-dihydrofuro[3,4-d]imidazole (formula II), resulting in a yield of 97%.

Workup

  1. filtrationfiltered
  2. washwashed
  3. concentrationThe filtrate was concentrated
  4. customacetone was recovered
  5. addition120 ml of ethyl acetate and 120 ml of water were added into the residual liquid, and pH
  6. customThe aqueous layer was separated
  7. extractionthe organic layer was further extracted with 20 ml×2 of water
  8. addition150 ml of ethyl acetate was added into the combined aqueous portion and pH
  9. additionSalt was added
  10. customthe organic layer was separated
  11. extractionThe aqueous layer was further extracted with 30 ml×2 of ethyl acetate
  12. dry with materialCombined organic portion was dried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a78dc6456d1640228620be1a65847b5c
Source dataset
uspto-grants-2013_12
Patent number
US08618308B2

Reaction notes

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