Reaction equation
ClC1C=CC2OC3C=CC=CC=3CN(C(O)=O)C=2C=1.Br[CH2:21][C:22]([NH:24][NH:25][C:26]([N:28]1[CH2:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[O:31][C:30]2[CH:39]=[CH:40][C:41]([Cl:43])=[CH:42][C:29]1=2)=[O:27])=[O:23].[CH2:44]([O:46][P:47]([O:51]CC)[O:48][CH2:49][CH3:50])[CH3:45].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>O1CCCC1.[Na+].[I-]>[CH2:44]([O:46][P:47]([CH2:21][C:22]([NH:24][NH:25][C:26]([N:28]1[CH2:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[O:31][C:30]2[CH:39]=[CH:40][C:41]([Cl:43])=[CH:42][C:29]1=2)=[O:27])=[O:23])([O:48][CH2:49][CH3:50])=[O:51])[CH3:45]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirring solution of 2.57 g (6.3 mmol) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2bromoacetyl) 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 Nal. 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 C20H23N23O6PCl (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
- temperatureAfter 22 hours of refluxing
- temperaturewas refluxed an additional 24 hours
- customThe solvent was then removed under aspirator vacuum
- customthe reaction mixture was chromatographed
Sources & evidence
- ORD record
- ord-18dfae63b19d4ed29008c60c1be364bb
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05182272
Linked notes
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