Sodium methanethiolate → Ethyl 2-(methylsulfanyl)-1,3-benzothiazole-6-carboxylate

HRID 1847990ノート

反応式

HRID 1847990 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:16][S-:17].[Na+]>C1COCC1>[CH3:16][S:17][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

参加物

4

反応物 2

HCID 4378561Sodium methanethiolateHCID 12067225Ethyl 2-bromo-6-benzothiazolecarboxylate

生成物 1

HCID 86680993Ethyl 2-(methylsulfanyl)-1,3-benzothiazole-6-carboxylate収率 84.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred mixture of 2-bromobenzo[d]thiazole-6-carboxylate (2.3 g, 7.9 mmol) from Step 1 of this Example in THF (15 mL) at 0° C. was added sodium thiomethoxide (607 mg, 8.7 mmol) in one portion. The mixture was allowed to warm to rt and stirred for 20 h. The mixture was partitioned between EtOAc (150 mL) and water (100 mL). The EtOAc layer was separated and washed with water (100 mL) and brine (100 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford ethyl 2-(methylthio)benzo[d]thiazole-6-carboxylate (1.7 g, 83%) as a yellow solid which did not require further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.69 (d, J=1.3 Hz, 1H), 8.02 (m, 1H), 7.92 (m, 1H), 4.35 (q, J=7.0 Hz, 2H), 2.83 (s, 3H), 1.35 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z 254 (M+H)+.

後処理

  1. customat 0° C.
  2. customThe mixture was partitioned between EtOAc (150 mL) and water (100 mL)
  3. customThe EtOAc layer was separated
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-aa77e699aa19423986fe23b007f81ee2
出典データセット
uspto-grants-2015_02
特許番号
US08952058B2

反応ノート

読み込み中…