Water → HCID 21915394, compound

HRID 1787523Notes

Reaction equation

HRID 1787523 reaction equation
O.[OH-].[K+].Br[C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[N:11][OH:12].COCCO>[Cu].ClCCl>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[C:6]3[S:7][CH:8]=[CH:9][C:5]=3[O:12][N:11]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 73853156HCID 73853156, compound

Product 1

HCID 21915394HCID 21915394, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Add to a solution of water (20 mL) and potassium hydroxide (7.2 g, 0.128 mol), (3-bromothiophen-2-yl)-(4-methoxyphenyl)-methanone oxime (19.6 g, 0.0628 mol) and 2-methoxyethanol (200 mL). Stir the solution and then treat under nitrogen with copper powder (1.0 g, 0.0157 g-atom 0.25 equiv.). Heat the stirred mixture to 60° C. for four hours, and then pour into a mixture of water (800 mL) and dichloromethane (450 mL). Add hydrochloric acid (10 mL, 6N), filter the mixture, and wash the copper with dichloromethane and water. Separate the filtrate, and wash the organic phase twice with water, dry (Na2SO4), filter and evaporate. Dissolve the residue in dichloromethane and chromatograph the compound over alumina, eluted with 4:1 heptane:dichloromethane, and then with 3:1 heptane:dichloromethane. Evaporate the fractions, triturate the residue with heptane, and collect the solid and dry at 60° C. to give the title compound (9.3 g, 64% yield), m.p. 93-94° C.

Workup

  1. filtrationAdd hydrochloric acid (10 mL, 6N), filter the mixture
  2. washwash the copper with dichloromethane and water
  3. customSeparate the filtrate
  4. washwash the organic phase twice with water
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. customevaporate
  8. dissolutionDissolve the residue in dichloromethane
  9. washchromatograph the compound over alumina, eluted with 4:1 heptane
  10. customEvaporate the fractions
  11. customtriturate the residue with heptane
  12. customcollect the solid
  13. customdry at 60° C.

Sources & evidence

ORD record
ord-457c641554e24a789e57e506250d6dfe
Source dataset
uspto-grants-2009_03
Patent number
US07511046B2

Reaction notes

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