Sodium Iodide → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(diethoxyphosphinyl)acetyl]hydrazide

HRID 1974524Notes

Reaction equation

HRID 1974524 reaction equation
Br[CH2:2][C:3]([NH:5][NH:6][C:7]([N:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12][C:11]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:10]1=2)=[O:8])=[O:4].[CH2:25]([O:27][P:28]([O:32]CC)[O:29][CH2:30][CH3:31])[CH3:26].[Na+].[I-]>O1CCCC1.[Na+].[I-]>[CH2:25]([O:27][P:28]([CH2:2][C:3]([NH:5][NH:6][C:7]([N:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12][C:11]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:10]1=2)=[O:8])=[O:4])([O:29][CH2:30][CH3:31])=[O:32])[CH3:26]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 31215Triethyl phosphite2×HCID 867465058-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-(bromoacetyl) hydrazide

Product 1

HCID 99562598-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(diethoxyphosphinyl)acetyl]hydrazideYield 83.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2.57 g (6.3 mmol) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-(bromoacetyl) hydrazide (19), prepared as described in Example 19 above, in 75 mL of tetrahydrofuran (THF) was added 1.25 g (7.5 mmol) of triethylphosphite and 0.15 g (1 mmol) of NaI. After 22 hours of refluxing, an additional 0.62 g (3.75 mmol) of triethylphosphite and 0.05 g (0.33 mmol) of NaI were added to the reaction, which was refluxed an additional 24 hours. The solvent was then removed under aspirator vacuum, and the reaction mixture was chromatographed to yield 2.46 g (83%) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(diethoxyphosphinyl)acetyl]hydrazide (20), which was a beige foam. Analysis calculated for C20H23N3O6PCl (M.W. 467.85): C, 51.35; H, 4.96; N, 8.98; Cl, 7.58. Found: C, 51.02; H, 5.03; N, 8.83; Cl, 7.39.

Workup

  1. temperatureAfter 22 hours of refluxing
  2. temperaturewas refluxed an additional 24 hours
  3. customThe solvent was then removed under aspirator vacuum
  4. customthe reaction mixture was chromatographed

Sources & evidence

ORD record
ord-86aba21eadf7419aba73e46863c1ca51
Source dataset
uspto-grants-1994_02
Patent number
US05283240

Reaction notes

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