Potassium Carbonate → Ethyl 3-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate

HRID 2276350Notes

Reaction equation

Cl[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]#[N:9].C(=O)([O-])[O-].[K+].[K+].[SH:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C.O1CCCC1>[NH2:9][C:8]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]=2[S:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-chlorocyclohex-1-enecarbonitrile (3.01 g; 21.3 mmol) in a mixture ethanol-tetrahydrofurane (6:1, 42 mL) were added potassium carbonate (3.12 g; 22.6 mmol) and ethyl 2-mercaptoacetate (3.5 mL; 31.9 mmol). The solution was heated under nitrogen atmosphere at 90° C. for 24 h. The solvent was evaporated under reduced pressure and the residue was purified by flash-chormatography on silica gel using a gradient of ethyl acetate (0-10%) in heptane as eluent to yield 2.4 g (50%) of ethyl 3-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate as a bright yellow solid. ESI/APCI (+): 226 (M+H).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by flash-chormatography on silica gel using a gradient of ethyl acetate (0-10%) in heptane as eluent

Sources & evidence

ORD record: ord-e911805d972a447198763a94a1d8e35e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132129B2

Reaction notes

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