Triethylamine → Ethyl 3-aminobenzo[b]thiophene-2-carboxylate

HRID 1358277Notes

Reaction equation

HRID 1358277 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][CH2:11][O:12][C:13]([CH2:15][SH:16])=[O:14].CCN(CC)CC>CS(C)=O>[NH2:5][C:4]1[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[S:16][C:15]=1[C:13]([O:12][CH2:11][CH3:10])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 678552-Fluorobenzonitrile

Product 1

HCID 731510Ethyl 3-aminobenzo[b]thiophene-2-carboxylateYield 70.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Fluorobenzonitrile (0.61 g, 5 mmol), ethyl thioglycollate (0.60 g, 5 mmol) and NEt3 (1.52 g, 15 mmol) are stirred in DMSO (5 mL) at 100° C. under N2 for 3 h. The reaction mixture is poured onto ice-water (50 mL), and the solid is collected by suction filtration, rinsed with water, and air dried to give ethyl 3-aminobenzothiophene-2-carboxylate (0.78 g, 70%) as a grey-brown solid. 1H NMR (DMSO) δ8.14 (1H, d, J=7.7 Hz), 7.88 (1H, d, J=8.1 Hz), 7.50 (1H, dt, Jd=1.2 Hz, Jt=7.5 Hz), 7.39 (1H, dt, Jd=1.2 Hz, Jt=7.6 Hz), 7.17 (2H, brs), 4.26 (2H, q, J=7.1 Hz), 1.29 (3H, t, J=7.1 Hz).

Workup

  1. additionThe reaction mixture is poured onto ice-water (50 mL)
  2. filtrationthe solid is collected by suction filtration
  3. washrinsed with water, and air
  4. customdried

Sources & evidence

ORD record
ord-79082443edfe4b7ab3904767acbf15c5
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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