Triethylamine → HCID 18184405, compound

HRID 1489597Notes

Reaction equation

HRID 1489597 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:13][CH2:14][O:15][C:16]([CH2:18][SH:19])=[O:17].CCN(CC)CC>CS(C)=O>[NH2:5][C:4]1[C:3]2[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=2[S:19][C:18]=1[C:16]([O:15][CH2:14][CH3:13])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 18184405HCID 18184405, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Fluoro-5-nitrobenzonitrile (1.664 g, 10 mmol), ethyl thioglycollate (1.21 g, 10 mmol) and NEt3 (3.06 g, 30 mmol) are stirred in DMSO (5 mL) at 100° C. under N2 for h h. The deep orange-red reaction mixture is poured onto ice-water (50 mL), and the solid is collected by suction filtration, rinsed with water, and dried in a vacuum oven at 60° C. to give ethyl 3-amino-5-nitrobenzothiophene-2-carboxylate (2.675 g, 100%) as a bright orange solid. 1H NMR (DMSO) δ9.23 (1H, d, J=2.1 Hz), 8.28 (1H, dd, J=2.3, 8.9 Hz), 8.10 (1H, d, J=9.0 Hz), 7.45 (2H, brs), 4.29 (2H, q, J=7.1 Hz), 1.30 (3H, t, J=7.1 Hz).

Workup

  1. additionThe deep orange-red reaction mixture is poured onto ice-water (50 mL)
  2. filtrationthe solid is collected by suction filtration
  3. washrinsed with water
  4. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-c97d43ec83174242a2b3e7698dbfbd5d
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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