Hydrochloric Acid → HCID 73886677, compound

HRID 844440Notes

Reaction equation

HRID 844440 reaction equation
[O-]CC.[Na+].[Na].[CH3:6][O:7][C:8]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O.[N:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N+:19]=[N-:20].Cl>O.C(O)C>[N:18]([C:21](=[CH:10][C:9]1[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:8]=1[O:7][CH3:6])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N+:19]=[N-:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 665812,3-DimethoxybenzaldehydeHCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 73886677HCID 73886677, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
-30 °C

Procedure

A sodium ethoxide solution, prepared using 80 ml of absolute ethanol and 2.76 g of sodium, is cooled to −30° C., under nitrogen. 4.99 g of 2,3-dimethoxybenzaldehyde and 15.5 g of ethyl azidoacetate are added and the mixture is then left stirring between −20° C. and −10° C. for 2 hours. The reaction medium is poured into 250 ml of water containing 25 ml of concentrated HCl. The precipitate formed is filtered off, washed with water and then dissolved in ether. This solution is dried over Na2SO4 and concentrated to give 5.86 g of the expected compound: m.p.<50° C.

Workup

  1. waitthe mixture is then left
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. dissolutiondissolved in ether
  6. dry with materialThis solution is dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de3f25ef7e7c4e128f27da4bf7b0fb91
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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