Diphenyl Ether → 3-(8-Chloro-dibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-ethoxy-3-cyclobutene-1,2-dione

HRID 1707577

Reaction equation

HRID 1707577 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=[N:10][C:4]=2[CH:3]=1.[CH2:17]([O:19][C:20]1[C:21](=O)[C:22](=[O:27])[C:23]=1[O:24]CC)[CH3:18].C1(OC2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][N:10]([C:21]3[C:22](=[O:27])[C:23](=[O:24])[C:20]=3[O:19][CH2:17][CH3:18])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 123228Diethyl squarateHCID 8382678-Chloro-dibenz[b,f]-[1,4]oxazepine

Product 1

HCID 152322933-(8-Chloro-dibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-ethoxy-3-cyclobutene-1,2-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-chloro-dibenz[b,f][1,4]oxazepine (2 g), 3,4-diethoxy-3-cyclobutene-1,2-dione (5 g), diphenylether (2 g) and dioxane (10 mL) was heated to reflux. After 2 hours, most of the dioxane was removed in vacuo and the precipitated title compound (0.75 g) was collected by filtration as yellow solid. The filtrate was treated with cold methanol when more of the title compound (1.2 g) precipitated. This material was used in Example 6 without further purification.

Workup

  1. temperaturewas heated to reflux
  2. custommost of the dioxane was removed in vacuo
  3. customthe precipitated title compound (0.75 g)
  4. filtrationwas collected by filtration as yellow solid
  5. additionThe filtrate was treated with cold methanol when more of the title compound (1.2 g)
  6. customprecipitated
  7. customThis material was used in Example 6 without further purification

Sources & evidence

ORD record
ord-57f9b35e48a04aa2872b5c7c2667e77f
Source dataset
uspto-grants-1994_10
Patent number
US05354746

Linked notes

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