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

HRID 1847958노트

반응식

HRID 1847958 반응식
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.CCOCC>[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

참가 물질

5

반응물 2

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

생성물 1

HCID 86680993Ethyl 2-(methylsulfanyl)-1,3-benzothiazole-6-carboxylate수율 98.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 2-bromobenzo[d]thiazole-6-carboxylate (4.8 g, 16.8 mmol) from Step 1 of Example 2 in THF (100 mL) was added sodium thiomethoxide (1.74 g, 25.2 mmol) slowly at 0° C. The reaction mixture was stirred at rt overnight. The mixture was diluted with Et2O (200 mL) and washed with saturated aq NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give ethyl 2-(methylthio)benzo[d]thiazole-6-carboxylate as a white solid (4.18 g, 98%). 1H NMR (300 MHz, CDCl3) δ 8.48 (d, J=1.5 Hz, 1H), 8.11 (dd, J=1.6, 8.6 Hz, 1H), 7.87 (d, J=8.5 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 2.82 (s, 3H), 1.42 (t, J=7.1 Hz, 3H) LCMS (ESI) m/z 254 (M+H)+.

후처리

  1. washwashed with saturated aq NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-11c3e78af3e540cea899ffd0b5e2db48
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952058B2

반응 노트

불러오는 중…