Sodium Bicarbonate → HCID 135760644, compound

HRID 2416614Notes

Reaction equation

HRID 2416614 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[O:10][CH2:11][C:12](=[O:22])[N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[N:14]=1.B(Br)(Br)Br.C(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[O:10][CH2:11][C:12](=[O:22])[N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[N:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 15516807HCID 15516807, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 135760644HCID 135760644, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (1000 ml) was dissolved 2-(2-methoxyphenyl)-4-(2-bromophenyl)-4H-1,3,4-oxadiazine-5(6H)-one (91.0 g) obtained in Example 17. Under ice-cooling, 1.0M boron tribromide/methylene chloride solution (900 ml) was added dropwise thereinto over 1 hour, followed by stirring for 1 hour. By adding an aqueous saturated sodium bicarbonate to the reaction solution, the organic layer was separated, and then purified by Cromatorex NH silica gel chromatography (methylene chloride). The resulting crude crystals were recrystallized from methylene chloride/hexane, to give the title compound (62.8 g, 74%).

Workup

  1. temperatureUnder ice-cooling
  2. customthe organic layer was separated
  3. custompurified by Cromatorex NH silica gel chromatography (methylene chloride)
  4. customThe resulting crude crystals were recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-1dfe2602a92f4bb4b9771b9578c035f1
Source dataset
uspto-grants-2004_11
Patent number
US06825192B1

Reaction notes

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