Acetic Acid → HCID 178452843, compound

HRID 470718Notes

Reaction equation

HRID 470718 reaction equation
[N-]=[N+]=[N-].[Na+].C(O)(=O)C.[N:9]1([C:18](=[NH:33])[N:19]2[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21][CH2:20]2)C2C=CC=CC=2[N:11]=[N:10]1>C(Cl)(Cl)Cl>[NH:33]1[C:18]([N:19]2[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21][CH2:20]2)=[N:9][N:10]=[N:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 68311086HCID 68311086, compound

Product 1

HCID 178452843HCID 178452843, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sodium azide (2.00 g, 30.7 mmol) and acetic acid (1.70 ml, 30.7 mmol) were added to a chloroform (300 ml) solution of the compound (10.6 g, 30.7 mmol) obtained in Step 1 above and the resulting mixture was stirred at room temperature for 25 hours. Insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography [chloroform:methanol=30:1→10:1 (v/v)] to give 8.20 g (94%) of the title compound as a solid.

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by silica gel column chromatography [chloroform:methanol=30:1→10:1 (v/v)]

Sources & evidence

ORD record
ord-45726adac83845f2aeaf72271b770307
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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