Hydrochloric Acid → Famoxadone

HRID 742091Notes

Reaction equation

HRID 742091 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:21])([OH:20])[C:15]([O:17]CC)=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([O:28]C2C=CC=CC=2)C=CC=CC=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:47]1([NH:53][NH2:54])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.Cl>O.C(O)(=O)C.C(Cl)Cl>[CH3:21][C:14]1([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:13][CH:12]=2)[O:20][C:22](=[O:28])[N:54]([NH:53][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:15]1=[O:17]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 7583Diphenyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 10859095Ethyl 2-(4-phenoxyphenyl)lactate2×

Product 1

HCID 213032FamoxadoneYield 81.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 14.3 g of ethyl 2-(4-phenoxyphenyl)lactate (34 g of a mixture containing 14.3 g of ethyl 2-(4-phenoxyphenyl)lactate and 19.7 g of diphenyl ether), 9.7 g of 1,1'-carbonyldiimidazole and 100 mL of methylene chloride was agitated at 25° C. for 19 h. Water (0.30 mL) was added and the mixture was agitated for 15 min. Then, 5 mL of acetic acid and 7.4 g of phenylhydrazine were added. After agitating at 25° C. for 24 h, 100 mL of water was added. The pH was lowered to 2 with hydrochloric acid, and the aqueous layer was removed. After washing the methylene chloride layer with 50 mL of water, the solvent was evaporated under vacuum. The oily residue was mixed with 150 mL hexane and 15 mL of ethyl acetate, heated to 65° C., cooled to 20° C., and then filtered. The solids were washed with 100 mL of a mixture of 20 mL ethyl acetate and 80 mL of hexane and then dried. The title product (15.2 g) was obtained with a m.p. of 137°-139° C.

Workup

  1. stirringthe mixture was agitated for 15 min
  2. stirringAfter agitating at 25° C. for 24 h
  3. customthe aqueous layer was removed
  4. washAfter washing the methylene chloride layer with 50 mL of water
  5. customthe solvent was evaporated under vacuum
  6. additionThe oily residue was mixed with 150 mL hexane and 15 mL of ethyl acetate
  7. temperatureheated to 65° C.
  8. temperaturecooled to 20° C.
  9. filtrationfiltered
  10. washThe solids were washed with 100 mL of a mixture of 20 mL ethyl acetate and 80 mL of hexane
  11. customdried

Sources & evidence

ORD record
ord-b9ac569619f746b6bb72144847c9a469
Source dataset
uspto-grants-1996_09
Patent number
US05552554

Reaction notes

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