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

HRID 1506511노트

반응식

HRID 1506511 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 58.2%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of methyl 4-amino-3-phenylisothiazole-5-carboxylate (Preparation 103C, 700 mg, 2.99 mmol) in chloroform (80 mL) were added iodine (4019 mg, 15.84 mmol) and amyl nitrite (0.602 mL, 4.48 mmol). The resulting mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and washed with aqueous sodium thiosulfate and then water. The organic layer was dried over sodium sulfate. Removal of the solvent in vacuo and crystallization from ethanol yielded methyl 4-iodo-3-phenylisothiazole-5-carboxylate (600 mg, 1.738 mmol, 58.2% yield) as a pale yellow solid. The compound had an LC/MS M+1=346.0.

후처리

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

출처 및 근거

ORD 기록
ord-6897a65a9f234ecab98806947d1450d7
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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