4-Nitrophenol → HCID 69883883, compound

HRID 866765Notes

Reaction equation

HRID 866765 reaction equation
ClC(OCC)=O.C(Cl)(Cl)Cl.[CH2:11]([C:14]1([C:23]([C:26]([OH:28])=[O:27])([CH3:25])[CH3:24])[C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16][C:15]1=[O:22])[CH:12]=[CH2:13].[CH:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31](O)[CH:30]=1>ClCCl.C(N(CC)CC)C>[CH2:11]([C:14]1([C:23]([C:26]([O:28][C:31]2[CH:30]=[CH:29][C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=2)=[O:27])([CH3:24])[CH3:25])[C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16][C:15]1=[O:22])[CH:12]=[CH2:13]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 6212ChloroformHCID 10928Ethyl chloroformateHCID 22743615HCID 22743615, compound

Product 1

HCID 69883883HCID 69883883, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 2.19 g. of ethyl chloroformate in 90 ml. of chloroform was added to a solution of 5.08 g. of "allonalcarboxylic acid" [5-allyl-5-(1-carboxyisopropyl)barbituric acid] and 2.02 g. of triethylamine in 100 ml. of dichloromethane, cooled to 0°-5°, and the mixture was stirred at room temperature for 5 hours. p-Nitrophenol (3.06 g.) was added and the mixture was stirred at room temperature for 14 hours. The reaction mixture was washed with saturated sodium carbonate solution (3 × 25 ml.), and water until the workings were neutral, dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate under reduced pressure gave 4.7 g. of an oil. Crystallization from a mixture of ether-heptane (1:1) gave 2.2 g. of the ester, m.p. 140°-141°.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. washThe reaction mixture was washed with saturated sodium carbonate solution (3 × 25 ml.), and water until the workings
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customEvaporation of the filtrate under reduced pressure
  6. customgave 4.7 g
  7. customCrystallization
  8. additionfrom a mixture of ether-heptane (1:1)
  9. customgave 2.2 g

Sources & evidence

ORD record
ord-fd61bd04db46403892f3e21ee53be4bf
Source dataset
uspto-grants-1978_07
Patent number
US04101549

Reaction notes

Loading…