Iodine → 5(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-iodophenyl)oxazolidin-2-one

HRID 1167496ノート

反応式

HRID 1167496 の反応式
[I:1]I.[S:3]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[O:14][C:13](=[O:15])[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11]2)=[N:4]1>C(#N)C.C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[S:3]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[O:14][C:13](=[O:15])[N:12]([C:16]3[CH:17]=[CH:18][C:19]([I:1])=[CH:20][CH:21]=3)[CH2:11]2)=[N:4]1

参加物

6

反応物 2

HCID 807IodineHCID 699806285(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one

生成物 1

HCID 699805285(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-iodophenyl)oxazolidin-2-one収率 73.4%

試薬・触媒・溶媒 3

HCID 76299Silver trifluoroacetate触媒HCID 6212Chloroform溶媒HCID 6342Acetonitrile溶媒

実験手順

Iodine (0.67 g, 2.64 mmol) was added portionwise to a stirred solution of 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one (0.7 g, 2.53 mmol) and silver trifluoroacetate (0.727 g, 3.29 mmol) in acetonitrile (4 ml) and chloroforrn (6 ml). The mixture was stirred for 24 hours in the dark. The mixture was filtered and the filtrate evaporated. The residue was extracted with EtOAc and the extract washed with water, dilute ammonia (0.1 ml of 0.88SG ammonia in 25 ml water), water and brine, dried (Na2SO4) and evaporated to give the title product as a solid (0.749 g, 73%)

後処理

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. extractionThe residue was extracted with EtOAc
  4. washthe extract washed with water, dilute ammonia (0.1 ml of 0.88SG ammonia in 25 ml water), water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-69288cb7e31449a7bc7378ee776070a1
出典データセット
uspto-grants-2003_09
特許番号
US06617339B1

反応ノート

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