Hydrochloric Acid → HCID 178438093, compound

HRID 2291607Notes

Reaction equation

HRID 2291607 reaction equation
[H-].[Na+].C(C1OC2C=CC=CC=2C=1C(=O)C1C=CC(O)=CC=1)C.ClCC#N.[CH2:27]([C:29]1[O:30][C:31]2[CH:49]=[CH:48][CH:47]=[CH:46][C:32]=2[C:33]=1[C:34]([C:36]1[CH:45]=[CH:44][C:39]([O:40][CH2:41][C:42]#[N:43])=[CH:38][CH:37]=1)=[O:35])[CH3:28].[N-:50]=[N+:51]=[N-:52].[Na+].Cl>CN(C=O)C.C1COCC1>[CH2:27]([C:29]1[O:30][C:31]2[CH:49]=[CH:48][CH:47]=[CH:46][C:32]=2[C:33]=1[C:34]([C:36]1[CH:45]=[CH:44][C:39]([O:40][CH2:41][C:42]2[NH:52][N:51]=[N:50][N:43]=2)=[CH:38][CH:37]=1)=[O:35])[CH3:28]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 33557Sodium AzideHCID 255968Methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)-HCID 15136005HCID 15136005, compound

Product 1

HCID 178438093HCID 178438093, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To an ice-water cooled suspension of NaH (0.18 g) in dry DMF (5 ml), is added a solution of a 2-ethyl-3-(4-hydroxybenzoyl)benzofuran, 1.00 g, in dry DMF 12 ml dropwise. After stirring for about 15 minutes running, chloroacetonitrile (0.24 ml) is added and heated up to 100° C. for 3 hours. After cooling to room temperature, the reaction mixture is poured over ice-water 100 ml and submitted to extraction by ethyl acetate. The solvent layer is washed by 10% NaOH solution and washed by NaCl solution and then dried by Na2CO3. Removing the solvent from the resulting solution gives a yellowish oily substance, that is 4-(2-ethyl-3-benzofuroyl)phenoxyacetonitrile. The obtained substance, in an amount of 1.05 g is dissolved in 15 ml of THF under an N2 gas stream. To this solution, aluminum chloride anhydride powder, 0.46 g, and then sodium azide, 0.98, are added and heated up to reflux for 24 hours. The reaction mixture is cooled by ice water and 10% HCl is added dropwise to make the solution acidic. After removal of THF, water is added and extracted by ethyl acetate (30 ml×2). The organic layer is washed by NaCl solution and dried over NaCO3. A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionsubmitted to extraction by ethyl acetate
  3. washThe solvent layer is washed by 10% NaOH solution
  4. washwashed by NaCl solution
  5. dry with materialdried by Na2CO3
  6. customRemoving the solvent from the resulting solution
  7. customgives a yellowish oily substance, that
  8. temperatureheated up
  9. temperatureto reflux for 24 hours
  10. additionis added dropwise
  11. customAfter removal of THF, water
  12. additionis added
  13. extractionextracted by ethyl acetate (30 ml×2)
  14. washThe organic layer is washed by NaCl solution
  15. dry with materialdried over NaCO3
  16. customA solid substance obtained
  17. customafter removal of the organic solvent
  18. customis recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-9f860178676c46bd9b4ab259b1c55145
Source dataset
uspto-grants-1989_01
Patent number
US04797415

Reaction notes

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