Hydrochloric Acid → HCID 67214764, compound

HRID 2421033Notes

Reaction equation

HRID 2421033 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[O-]CC.[Na+].[Na].[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([CH2:20][N:21]=[N+:22]=[N-:23])=[CH:18][CH:17]=1.Cl>C(O)C.O>[NH2:2][C:1]1[N:21]([CH2:20][C:19]2[CH:24]=[CH:25][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[N:22]=[N:23][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 109317671-(Azidomethyl)-4-methoxybenzene

Product 1

HCID 67214764HCID 67214764, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Ethyl cyanoacetate (1.96 mL) was added to a solution of sodium ethoxide, prepared from sodium (0.423 g) and ethanol (45 mL), and the solution was stirred for 30 min. A solution of 4-methoxybenzylazide (3.0 g) in ethanol (5 mL) was added dropwise and the mixture was heated under reflux for 5 h. The cooled mixture was poured into water and acidified with dilute hydrochloric acid then extracted with ethyl acetate. The extracts were washed with water, brine and evaporated. Purification by flash chromatography (ethyl acetate/dichloromethane 1:9 then 15:85) gave the product as a pale yellow solid (0.85 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 h
  3. extractionthen extracted with ethyl acetate
  4. washThe extracts were washed with water, brine
  5. customevaporated
  6. customPurification by flash chromatography (ethyl acetate/dichloromethane 1:9

Sources & evidence

ORD record
ord-5fdd58079989465fb535b41cc9372050
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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