Ethyl cyanoformate → HCID 21530644, compound

HRID 1657864Notes

Reaction equation

HRID 1657864 reaction equation
[N:1]([CH2:4][C:5]([OH:7])=[O:6])=[N+:2]=[N-:3].[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:9]>>[CH2:13]([O:12][C:10]([C:8]1[N:1]([CH2:4][C:5]([OH:7])=[O:6])[N:2]=[N:3][N:9]=1)=[O:11])[CH3:14]

Participants

3

Reactant 2

HCID 69336Ethyl cyanoformateHCID 155605Azidoacetic acid

Product 1

HCID 21530644HCID 21530644, compound

Conditions

Temperature
110 °C

Procedure

A mixture of azidoacetic acid (5.0 grams, 50 mmol.) and ethyl cyanoformate (15.0 grams, 150 millimoles,) was heated at 110°C. for 8.5 hours. The reaction mixture was cooled; crystalline product separated which was filtered and washed with toluene. The filtrate was concentrated under vacuum, and the remaining oil was cooled and seeded with a crystal of the product to give a second crop. The yield of the title product was 5.1 grams (51 percent, assuming pure starting materials), m.p. (both crops) 144°-147°C. The analysis was as follows:

Workup

  1. temperatureThe reaction mixture was cooled
  2. customcrystalline product separated which
  3. filtrationwas filtered
  4. washwashed with toluene
  5. concentrationThe filtrate was concentrated under vacuum
  6. temperaturethe remaining oil was cooled
  7. customto give a second crop

Sources & evidence

ORD record
ord-cf7662d76d164136bc53eb659396363b
Source dataset
uspto-grants-1976_06
Patent number
US03962272

Reaction notes

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