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

HRID 1506511ノート

反応式

HRID 1506511 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 58374164Methyl 4-iodo-3-phenylisothiazole-5-carboxylate収率 58.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6897a65a9f234ecab98806947d1450d7
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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