Tetrahydrofuran → HCID 2889802, compound

HRID 1589183Notes

Reaction equation

HRID 1589183 reaction equation
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O1CCCC1.[N:29]1([CH2:34][CH2:35][CH2:36][NH2:37])[CH:33]=[CH:32][N:31]=[CH:30]1>O>[N:29]1([CH2:34][CH2:35][CH2:36][NH:37][C:1](=[O:11])[CH:2]=[CH:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 787361H-Imidazole-1-propanamineHCID 444539Cinnamic Acid

Product 1

HCID 2889802HCID 2889802, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.22 g. of trans-cinnamic acid, 2.43 g, of 1,1'-carbonyldiimidazole and 50 ml. of tetrahydrofuran was stirred for 2 hours, then 1.7 ml. of 1H-imidazole-1-propanamine was added. The reaction mixture was stirred for 18 hours, then 5 ml. of water was added, the mixture was heated for 30 minutes and then concentrated. Methylene chloride and 10 ml. of 1N sodium hydroxide were added and then layers were separated. The organic layer was washed with water, dried over magnesium sulfate and concentrated, giving the desired product as a viscous oil.

Workup

  1. additionA mixture of 2.22 g
  2. temperaturethe mixture was heated for 30 minutes
  3. concentrationconcentrated
  4. additionof 1N sodium hydroxide were added
  5. customlayers were separated
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0d82d48b55c24a2e950d6aee0f51b6f7
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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