Potassium Carbonate → methyl 3-amino-5-nitro-1-benzothiophene-2-carboxylate

HRID 235062Notes

Reaction equation

HRID 235062 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[C:13]([O:17][CH2:18]C)(=[O:16])[CH2:14][SH:15].C([O-])([O-])=O.[K+].[K+]>C(O)C>[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:15][C:14]=1[C:13]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 2759774methyl 3-amino-5-nitro-1-benzothiophene-2-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-5-nitrobenzonitrile (25.0 g, 136.9 mmol), commercially available, was treated with 1 equivalent ethyl thioglycolate and 1 equivalent K2CO3 in ethanol by the procedure described in Example 41A to yield the title compound (19.68 g, 54%). m.p. 208°-210° C. 1H NMR(300MHz, DMSO) δ9.23 (d, 1H), 8.29 (d, 1H), 8.11 (dd, 1H), 7.45 (br s, 2H), 4.29 (q, 2H), 1.31 (t, 3H). MS (DCI/NH3) m/e 284 (M+NH4)+.

Sources & evidence

ORD record
ord-186ea6bd9f1e4086aadab605c84830e3
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

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