Acetic acid, azido-, ethyl ester → HCID 86628020, compound

HRID 2095263Notes

Reaction equation

HRID 2095263 reaction equation
[O-]CC.[Na+].[Br:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:14])=[C:10]([CH:13]=1)[CH:11]=O.[N:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N+:16]=[N-:17]>C(O)C.C(O)C.O1CCCC1>[N:15](/[C:18](=[CH:11]\[C:10]1[CH:13]=[C:6]([Br:5])[CH:7]=[CH:8][C:9]=1[Cl:14])/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N+:16]=[N-:17]

Participants

6

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxideHCID 106089255-Bromo-2-chlorobenzaldehyde

Product 1

HCID 86628020HCID 86628020, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of sodium ethoxide in ethanol (15 mL) cooled to −10° C. was added dropwise a solution of 5-bromo-2-chlorobenzaldehyde (1.0 g) and ethyl 2-azidoacetate (11 mL, 18 mmol) in ethanol-tetrahydrofuran (15 mL-3 mL). The reaction mixture was stirred at −10° C. for 3 hours, allowed to warm to 10° C. over 3 hours and poured onto crushed ice. The solid was collected by filtration and dried in a vacuum oven to provide the title compound.

Workup

  1. temperatureto warm to 10° C. over 3 hours
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe solid was collected by filtration
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-145da0e072844bf39bf8c73895bfebaa
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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