Acetic Acid → HCID 45280747, compound

HRID 473498Notes

Reaction equation

HRID 473498 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][C:23]([NH2:25])=[CH:24][C:17]=3[CH2:16][O:15][C:14]=2[CH:26]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[CH:31](OC)(OC)OC.C(O)(=O)C>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][C:23]([N:25]4[CH:31]=[N:29][N:28]=[N:27]4)=[CH:24][C:17]=3[CH2:16][O:15][C:14]=2[CH:26]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 33557Sodium AzideHCID 45280696HCID 45280696, compound

Product 1

HCID 45280747HCID 45280747, compound

Conditions

Temperature
100 °C

Procedure

0.015 g (0.042 mmol) of (8) and 0.01 g (0.15 mmol) of sodium azide are suspended in 0.05 g (0.33 mmol) of trimethyl orthoformate at 0° C. 0.03 g (0.50 mmol) of glacial acetic acid is then added to the mixture and the mixture is heated to 100° C. and refluxed for 4 h. After cooling to room temperature, the mixture is concentrated in vacuo and the residue is taken up with EtOAc and dissolved under the influence of heat. The yellow product precipitates out in the cold.

Workup

  1. temperaturerefluxed for 4 h
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture is concentrated in vacuo
  4. dissolutiondissolved under the influence
  5. temperatureof heat
  6. customThe yellow product precipitates out in the cold

Sources & evidence

ORD record
ord-d3fd13324f2f44de9fc4ca2a275c9ce2
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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