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

HRID 51219

반응식

HRID 51219 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bc5d0e561d0248559f5605bfeb83b1ff
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713629B2

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