2-Chlorobenzaldehyde → HCID 53962035, compound

HRID 1249926Notes

Reaction equation

HRID 1249926 reaction equation
[Na].[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[N:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N+:12]=[N-:13]>CO>[N:11]([C:14](=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[Cl:2])[C:15]([O:17][CH3:18])=[O:16])=[N+:12]=[N-:13]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 4020482Methyl 2-azidoacetateHCID 5360545Sodium

Product 1

HCID 53962035HCID 53962035, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-18 °C

Procedure

Sodium pieces(3.678 g, 160 mmol) were added in portions to methanol (200 ml) over a 30 minute period. The resulting solution was cooled in a dry ice/acetone bath to −18° C. and then over one hour a mixture of 2-chlorobenzaldehyde (4.832 g, 40 mmol) and methyl azidoacetate (160 mmol) was added at a rate that maintained the temperature below −15° C. After three hours, the solution was stored at 5° C. for two days to give crystalline material which was collected by filtration and washed with cold hexane to give pure product as a yellow crystals.

Workup

  1. additionwas added at a rate that
  2. temperaturemaintained the temperature below −15° C
  3. waitthe solution was stored at 5° C. for two days
  4. customto give crystalline material which
  5. filtrationwas collected by filtration
  6. washwashed with cold hexane
  7. customto give pure product as a yellow crystals

Sources & evidence

ORD record
ord-bcce1393728145a0ae01966359ce7825
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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