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Hydrochloric Acid → Famoxadone

HRID 742091
ノート
印刷プレビュー

反応式

HRID 742091 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

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

生成物 1

HCID 213032Famoxadone収率 81.3%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒
HCID 962Water溶媒2 回
HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b9ac569619f746b6bb72144847c9a469
出典データセット
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05552554

反応ノート

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