Chloroacetanilide → HCID 178457010、化合物

HRID 2115208

反応式

HRID 2115208 の反応式
[H-].[Na+].[CH2:3]([N:6]=[C:7]=[S:8])[CH2:4][CH3:5].Cl[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].C(OCC)C.CCCCCC>CN(C=O)C>[C:14]1([N:13]2[C:11](=[O:12])[CH2:10][S:8]/[C:7]/2=[N:6]\[CH2:3][CH2:4][CH3:5])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 11485ChloroacetanilideHCID 24758Sodium hydrideHCID 69403Propyl IsothiocyanateHCID 21584099Diethylether hexane

生成物 1

HCID 178457010HCID 178457010、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

At rt, NaH (154 mg of 55% dispersion in mineral oil, 3.54 mmol) is added in portions to a solution of n-propylisothiocyanate (596 mg, 5.90 mmol) and the above 2-chloro-N-phenyl-acetamide (1000 mg, 5.90 mmol) in DMF (30 mL). Stirring is continued for 2 h after completion of the addtion. The mixture is poured onto EA (150 mL) and is extracted twice with 1 N aq. HCl (200 mL). The aq. layer is neutralised by adding 3 N NaOH followed by sat. aq. NaHCO3, and extracted twice with EA (200 mL). The organic extracts are washed with water (200 mL) and evaporated to give a pale yellow, crystalline solid. This material is suspended in a small amount of diethyl ether/hexane 1:1, filtered, washed with additional diethyl ether/hexane and dried under high vacuum to give 3-phenyl-2-[(Z)-propylimino]-thiazolidin-4-one.

後処理

  1. additionThe mixture is poured onto EA (150 mL)
  2. extractionis extracted twice with 1 N aq. HCl (200 mL)
  3. additionby adding 3 N NaOH
  4. extractionextracted twice with EA (200 mL)
  5. washThe organic extracts are washed with water (200 mL)
  6. customevaporated
  7. customto give a pale yellow, crystalline solid
  8. filtrationfiltered
  9. washwashed with additional diethyl ether/hexane
  10. customdried under high vacuum

出典と根拠

ORDレコード
ord-eb2eef040fa84f059968887c35e985cd
出典データセット
uspto-grants-2008_10
特許番号
US07435828B2

関連ノート

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