2-[[(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10yl)-carbonyl]amino]-N-methoxy-N-methylacetamide → 8-chloro-N-(2-oxo-3-butenyl)dibenz-[b,f][1,4]oxazepin-10(11H)-carboxamide

HRID 1975680Notes

Reaction equation

HRID 1975680 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[O:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15](N(OC)C)=[O:16])=[O:12])[C:4]=2[CH:3]=1.C(=O)=O.[CH3:30][C:31](C)=O.C([Mg]Br)=C>O1CCCC1>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[O:6][C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15](=[O:16])[CH:30]=[CH2:31])=[O:12])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 105715372-[[(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10yl)-carbonyl]amino]-N-methoxy-N-methylacetamideHCID 18522661Acetone cardiceHCID 178418507HCID 178418507, compound

Product 1

HCID 108311978-chloro-N-(2-oxo-3-butenyl)dibenz-[b,f][1,4]oxazepin-10(11H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-[[(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10yl)-carbonyl]amino]-N-methoxy-N-methylacetamide (3.2 grams) in anhydrous tetrahydrofuran (35 mL) at -70° C. (dry ice/acetone bath) under a nitrogen atmosphere was added dropwise a solution of vinylmagnesium bromide (1.0M in tetrahydrofuran; 28 mi) in tetrahydrofuran (15 mL). The ice bath was removed, and the reaction was stirred to room temperature for one hour. The reaction was poured into 1M NaH2PO4 (250 mL) and extracted with ethyl acetate (3×200 mL). The combined ethyl acetate extracts were washed with 1M NaH2PO4 (2×250 mL) and brine (250 mL), dried over MgSO4, and evaporated in vacuo. The crude product was purified by flash chromatography through silica gel 60 (500 mL) using 9:1 methylene chloride:ethyl acetate to yield a colorless glass. The yield of the title compound was 2.25 grams (77%).

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was poured into 1M NaH2PO4 (250 mL)
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe combined ethyl acetate extracts were washed with 1M NaH2PO4 (2×250 mL) and brine (250 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash chromatography through silica gel 60 (500 mL)
  8. customethyl acetate to yield a colorless glass

Sources & evidence

ORD record
ord-01412e1f15174fc8be84e275b50321dc
Source dataset
uspto-grants-1994_02
Patent number
US05288719

Reaction notes

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