Ethyl cyanoacetate → Ethyl (1,3-benzothiazol-2-yl)acetate

HRID 1160648Notes

Reaction equation

HRID 1160648 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#N>>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

3

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 87132-Aminothiophenol

Product 1

HCID 359796Ethyl (1,3-benzothiazol-2-yl)acetateYield 72%

Conditions

Temperature
120 °C

Procedure

Ethyl 2-(benzothiazol-2-yl)acetate was prepared by the method of Abbotto, Bradamante et. al. ( J. Org. Chem. 2002, 16, 5753). A neat mixture of 2-aminothiophenol (6.94 g, 50 mmol) and ethyl cyanoacetate (5.65 g, 50 mmol) was heated at 120° C. for 3 hours at which time TLC analysis indicated that the reaction was complete as judged by the disappearance of starting material. The dark orange mixture was diluted with ethyl acetate/hexanes and purified by flash chromatography using 10-20% ethyl acetate/hexanes (Rf0.35, 10% ethyl acetate/hexanes) as an eluant. After concentration by rotary evaporator, ethyl 2-(benzothiazol-2-yl)acetate could be obtained as a yellow oil in 72% yield (7.97 g). LCMS: 222.3 (M+H)+.

Workup

  1. custompurified by flash chromatography
  2. concentrationAfter concentration
  3. customby rotary evaporator, ethyl 2-(benzothiazol-2-yl)acetate
  4. customcould be obtained as a yellow oil in 72% yield (7.97 g)

Sources & evidence

ORD record
ord-4b5958bbac904daa8dae0ac5cc9c54da
Source dataset
uspto-grants-2010_10
Patent number
US07816524B2

Reaction notes

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