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

HRID 1847958Notes

Reaction equation

HRID 1847958 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-11c3e78af3e540cea899ffd0b5e2db48
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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