Chloride → HCID 14719524, compound

HRID 1723339Notes

Reaction equation

HRID 1723339 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:12]2[CH:22]=[C:23]([OH:28])[C:24]([OH:27])=[C:25]([Cl:26])[C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl-].O.CN([CH:36]=[O:37])C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH:13]([C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)[C:12]2[CH:22]=[C:23]([OH:28])[C:24]([O:27][CH2:10][C:11]3[CH:25]=[CH:24][C:23]([O:37][CH3:36])=[CH:22][CH:12]=3)=[C:25]([Cl:26])[C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 312ChlorideHCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 14719518HCID 14719518, compound

Product 1

HCID 14719524HCID 14719524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g of 3-t-butyloxycarbonyl-6-chloro-7, 8-dihydroxy-1-(4'-hydroxyphenyl) 2,3,4,5-tetrahydro-1H-3-benzazepine was dissolved in 100 ml of DMF. To this was added 1.25 g of a 50% sodium hydride mineral oil dispersion under an argon atmosphere. The reaction was stirred at ambient temperature for 15 minutes and 3.59 g of 4-methozybenyl chloride was added. The reaction was stirred for 16 hours at ambient temperature then poured into a large volume of water. The mixture was then extracted with ethyl acetate. The extracts were washed with water dried over magnesium sulfate and concentrated to yield an oil. The crude product was dissolved in 100 ml. of acetonitrile and the solution washed with several portions of petroleum ether. The acetonitrile solution was concentrated and seeded with crystals of the product. The solution was allowed to stand in a freezer overnight with a resultant of white solid. Additional solid was obtained after concentration of the mother liquor. The solid (5.57 g) was heated for 10 minutes in 100 ml of dichloromethane on a steam bath. The suspension was filtered and the solid washed with warm dichloromethane to yield 3-t-butyloxycarbonyl-6-chloro-8-hydroxy-7-(4-methoxybenzyloxy)-1-(4 -hydroxyphenyl)-2,3,4,5 tetrahydro-1-H-3-benzazepine, M.P. 190°-192° C.

Workup

  1. stirringThe reaction was stirred for 16 hours at ambient temperature
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto yield an oil
  7. washof acetonitrile and the solution washed with several portions of petroleum ether
  8. concentrationThe acetonitrile solution was concentrated
  9. waitto stand in a freezer overnight with a resultant of white solid
  10. customAdditional solid was obtained after concentration of the mother liquor
  11. filtrationThe suspension was filtered
  12. washthe solid washed with warm dichloromethane

Sources & evidence

ORD record
ord-485642fa6e2047f7a1b73798d3d8c7fb
Source dataset
uspto-grants-1989_08
Patent number
US04861771

Reaction notes

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