Hydrochloric Acid → HCID 11393256, compound

HRID 1743322Notes

Reaction equation

HRID 1743322 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])O[C:8]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:7][C:6]=2[CH:16]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].Cl>[Cl-].[Na+].O.CCCCCC.C(O)CO.O.C1(C)C=CC=CC=1>[CH2:17]([N:24]1[C:10](=[O:11])[C:5]2[C:6](=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:7]=[C:8]1[CH2:12][CH:13]([CH3:15])[CH3:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 22238800HCID 22238800, compound

Product 1

HCID 11393256HCID 11393256, compoundYield 82.8%

Reagents, catalysts & solvents 5

HCID 174Ethylene GlycolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
115 °C

Procedure

A flask, equipped with an overhead stirrer, heating mantle, condenser and Dean-Stark apparatus was charged with 1,500 mL of toluene, 412.7 g (1 eq.) of 7-chloro-2-isobutyl-benzo[d][1,3]oxazin-4-one and 281.0 g (1.5 eq.) of benzylamine and brought to reflux for 3 hours. After removal of the water, ethylene glycol (150 mL) and 14.2 g (0.2 eq.) of NaOH were added and the mixture was heated to 115° C. for 5 hours. Completion of the reaction was monitored by TLC, after which the temperature was cooled to 60° C. and the pH adjusted to about 7 with 1N HCl, followed by the addition of 1 L of brine. The top organic layer was separated and the aqueous layer extracted with methylene chloride (2×300 mL). The organic phases were combined and dried over sodium sulfate. Solvents were stripped off leaving a viscous oil to which warm hexane (500 mL) was added. The mixture was cooled in an ice bath to give white crystals, which were separated by filtration. The filter cake was washed with cold hexane (800 mL) and air dried to give the title product as a white solid (470 g). An additional 42.4 g of title product was obtained from the mother liquor (512.4 g, 90.3%).

Workup

  1. customA flask, equipped with an overhead stirrer
  2. temperatureheating mantle, condenser and Dean-Stark apparatus
  3. temperatureto reflux for 3 hours
  4. additionwere added
  5. temperatureafter which the temperature was cooled to 60° C.
  6. customThe top organic layer was separated
  7. extractionthe aqueous layer extracted with methylene chloride (2×300 mL)
  8. dry with materialdried over sodium sulfate
  9. customleaving a viscous oil to which
  10. additionwas added
  11. temperatureThe mixture was cooled in an ice bath
  12. customto give white crystals, which
  13. customwere separated by filtration
  14. washThe filter cake was washed with cold hexane (800 mL) and air
  15. customdried

Sources & evidence

ORD record
ord-c32e418be9bb4b5ead1c2f184cbd5d60
Source dataset
uspto-grants-2006_03
Patent number
US07009049B2

Reaction notes

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