Diethyl Ether → HCID 67358795, compound

HRID 1668345Notes

Reaction equation

HRID 1668345 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[Br:9][C:10]1[C:24]([F:25])=[CH:23][C:13]2[O:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[CH:17]=[N:18][C:12]=2[CH:11]=1.CCOCC>C1(C)C(C)=CC=CC=1>[Br:9][C:10]1[C:24]([F:25])=[CH:23][C:13]2[O:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C@H:17]3[C@H:2]([C:1]([OH:7])=[O:8])[CH2:3][CH2:4][C:5](=[O:6])[N:18]3[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7940Glutaric anhydrideHCID 67357718HCID 67357718, compound

Product 1

HCID 67358795HCID 67358795, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

Glutaric anhydride (7.2 g, 63 mmol) was added to a stirred solution of 8-bromo-7-fluoro-dibenz[b,f][1,4]oxazepine (46.5 mmol) in xylene (26 mL) and the mixture was heated to 140° C. for 120 h. The reaction mixture was allowed to cool to ambient temperature, ether was added and the solution extracted (3×) with 2M NaOH. The pH of the combined extracts was adjusted to pH 4 by adding 3M hydrochloric acid. The product was collected by filtration and dried to yield the title compound (14.1 g, 81%) which was used without further purification. 1H-NMR (400 MHz, CDCl3) 2.03-2.14 (m, 1H), 2.31-2.4 (m, 1H), 2.53-2.62 (m, 1H), 2.67-2.81 (m, 1H), 3.55-3.60 (m, 1H), 5.46-5.49 (m, 1H), 7.05-7.09 (d, J=8.6, 1H), 7.11-7.32 (m, 4H), 7.56-7.59 (d, J=7.8, 1H). (m/z)=406+408 (M+H)+.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthe solution extracted (3×) with 2M NaOH
  3. additionby adding 3M hydrochloric acid
  4. filtrationThe product was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-3b3e3f9d071c4c8cbeb2e97232f15b49
Source dataset
uspto-grants-2011_08
Patent number
US07989442B2

Reaction notes

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