Methyl iodide → 5-Bromo-2-(methylthio)benzo[d]thiazole

HRID 1972985노트

반응식

HRID 1972985 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.[CH2:12]1COCC1.IC.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:12])=[N:7][C:6]=2[CH:11]=1

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 178527757HCID 178527757, 화합물

생성물 1

HCID 28012715-Bromo-2-(methylthio)benzo[d]thiazole수율 76%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 5-bromo-1,3-benzothiazole-2-thiol (3.0 g, 12.19 mmol), dry THF (44 mL), iodomethane (0.80 mL, 12.80 mmol), KOH (0.68 g, 12.19 mmol), and tetra-n-butylammonium bromide (0.39 g, 1.2 mmol) was stirred at rt overnight. The reaction mixture was diluted with EtOAc (100 mL) and washed with saturated, aqueous Na2CO3 (50 mL). The organic layer was dried over MgSO4 and then concentrated. The crude material was purified by ISCO® chromatography using 1-2% EtOAc in hexane to obtain the desired product (2.4 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ 8.02 (s, 1H), 8.0 (d, 1H), 7.51 (d, 1H), 2.79 (s, 3H); LC-MS m/z[M+H]+ 260.3 & 262.2, RT 3.82 min.

후처리

  1. washwashed with saturated, aqueous Na2CO3 (50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude material was purified by ISCO® chromatography

출처 및 근거

ORD 기록
ord-4a4069f37ac4492fba1b39e70e9aca41
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431695B2

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