Dichloromethane → 2-Hydroxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidine-4-one

HRID 51219

反応式

HRID 51219 の反応式
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6][C:5](=S)[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].C(Cl)Cl.F[B-](F)(F)F.C([O+](CC)CC)C.Cl.[NH2:38][OH:39]>CO.C(N(CC)CC)C>[OH:39][N:38]=[C:5]1[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3](=[O:15])[C:2]([CH3:1])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6]1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 2723982Triethyloxonium tetrafluoroborateHCID 120563925-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one

生成物 1

HCID 865884972-Hydroxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidine-4-one収率 70.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

実験手順

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one (0.3 g) was added to a 1M methylene chloride solution of triethyloxonium tetrafluoroborate (1 ml) at room temperature with stirring. After stirring the mixture for 24 hrs hydroxylamine hydrochloride (0.1 g) and triethylamine (0.3 g) in methanol (10 ml) were added at 0° C. The reaction mixture was again stirred for 2 hrs at room temperature followed by evaporation of the solvents under reduced pressure. The residue was added to ice water and then extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous ethyl acetate and the solvent was then evaporated under reduced pressure. The residue was purified by column chromatography (ethyl acetate-n-hexane, ½) to yield 2-hydroxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidine-4-one (0.21 g) having a melting point of 62-63° C.

後処理

  1. additionwere added at 0° C
  2. stirringThe reaction mixture was again stirred for 2 hrs at room temperature
  3. customfollowed by evaporation of the solvents under reduced pressure
  4. additionThe residue was added to ice water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried over anhydrous ethyl acetate
  7. customthe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by column chromatography (ethyl acetate-n-hexane, ½)

出典と根拠

ORDレコード
ord-bc5d0e561d0248559f5605bfeb83b1ff
出典データセット
uspto-grants-2004_03
特許番号
US06713629B2

関連ノート

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