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

HRID 1972985ノート

反応式

HRID 1972985 の反応式
[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

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 178527757HCID 178527757、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a4069f37ac4492fba1b39e70e9aca41
出典データセット
uspto-grants-2013_04
特許番号
US08431695B2

反応ノート

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