Methyl iodide → 6-Iodo-2-(methylthio)benzo[d]thiazole

HRID 1848110노트

반응식

HRID 1848110 반응식
[I:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI>C1COCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([S:9][CH3:12])[S:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178527793HCID 178527793, 화합물

생성물 1

HCID 669058856-Iodo-2-(methylthio)benzo[d]thiazole수율 76.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred mixture of 6-iodobenzo[d]thiazole-2-thiol (0.5 g, 1.7 mmol) and potassium carbonate (0.23 g, 1.7 mmol) in THF (10 mL) was added methyl iodide (0.12 mL, 1.1 mmol). After stirring at rt overnight, the mixture was concentrated under reduced pressure to give a solid. The solid was partitioned between saturated aq sodium carbonate and DCM. The organic layer was dried over Na2SO4 and filtered, and concentrated under reduced pressure to give 6-iodo-2-(methylthio)benzo[d]thiazole as a off-white solid (0.4 g, 76%). 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J=1.2 Hz, 1H), 7.69 (dd, J=1.8, 8.4 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 2.78 (s, 3H). LCMS (ESI) m/z 308 (M+H)+.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give a solid
  3. customThe solid was partitioned between saturated aq sodium carbonate and DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-eb2e477d784342fc9bce7862411b7df7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952058B2

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