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

HRID 1422985

Reaction equation

HRID 1422985 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+].[CH2:16]([O:18][C:19](=[O:22])[CH2:20][SH:21])[CH3:17]>CCO.C1COCC1>[CH2:16]([O:18][C:19]([C:20]1[S:21][C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:8]=1[NH2:9])=[O:22])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 498409392-Chlorocyclohex-1-ene-1-carbonitrile

Product 1

HCID 312340Ethyl 3-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylateYield 101.4%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
90 °C

Procedure

A 250 mL flask was charged with 2-chloro-cyclohex-1-enecarbonitrile (3.0 g, 21 mmol) in a 6:1 mixture of EtOH/THF (42 mL), K2CO3 (2.9 g, 21 mmol), and mercapto-acetic acid ethyl ester (3.5 mL, 32 mmol), after which it was fitted with a reflux condenser under N2 atmosphere and heated to 90° C. for 24 h. The mixture was filtered through a pad of diatomaceous earth, such as Celite®, rinsing thoroughly with MeOH (400 mL). After concentration, the title compound was purified by FCC (60% ethyl acetate (EtOAc)/hexanes) to give an amber-colored oil (4.8 g). MS: 226.1. 1H NMR (400 MHz, CDCl3) δ ppm 5.35 (s, 2H), 2.71-2.64 (m, 2H), 2.36-2.26 (m, 2H), 1.87-1.77 (m, 4H), 1.33 (t, J=7.1 Hz, 3H).

Workup

  1. customafter which it was fitted with a reflux condenser under N2 atmosphere
  2. filtrationThe mixture was filtered through a pad of diatomaceous earth, such as Celite®
  3. washrinsing thoroughly with MeOH (400 mL)
  4. concentrationAfter concentration
  5. customthe title compound was purified by FCC (60% ethyl acetate (EtOAc)/hexanes)

Sources & evidence

ORD record
ord-8220db8d632e4987a18fbcdf3513ba4a
Source dataset
uspto-grants-2015_01
Patent number
US08927555B2

Linked notes

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