Iodine → Methyl 4-iodo-3-phenylisothiazole-5-carboxylate

HRID 1948543노트

반응식

HRID 1948543 반응식
N[C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[I:17]I.N(OCCCCC)=O>C(Cl)(Cl)Cl>[I:17][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 807IodineHCID 10026Pentyl nitriteHCID 13073192Methyl 4-amino-3-phenyl-1,2-thiazole-5-carboxylate

생성물 1

HCID 58374164Methyl 4-iodo-3-phenylisothiazole-5-carboxylate수율 40.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of methyl 4-amino-3-phenylisothiazole-5-carboxylate (500 mg, 2.134 mmol) in chloroform (15 mL) was added iodine (287 mg, 11.31 mmol) and amyl nitrite (0.430 mL, 3.20 mmol). The resulting mixture was heated at reflux for 30 min., cooled to room temperature, washed with aqueous sodium thiosulfate and water. The organic layer was dried over Na2SO4. Removal of the solvent in vacuo and crystallization from ethanol yielded methyl 4-iodo-3-phenylisothiazole-5-carboxylate (300 mg, 0.869 mmol, 40.7% yield) as a pale yellow solid.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 30 min.
  3. washwashed with aqueous sodium thiosulfate and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customRemoval of the solvent
  6. customin vacuo and crystallization from ethanol

출처 및 근거

ORD 기록
ord-ca52ce27c9984085a16bfad3726c8157
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399451B2

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