Methyl 5-chloro-4-nitrothiophene-2-carboxylate → Methyl 5-((3,5-dichloro-2,6-dimethylpyridin-4-yl)thio)-4-nitrothiophene-2-carboxylate

HRID 1192249Notes

Reaction equation

HRID 1192249 reaction equation
Cl[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Cl:14][C:15]1[C:16]([CH3:24])=[N:17][C:18]([CH3:23])=[C:19]([Cl:22])[C:20]=1[S-:21].[Na+]>>[Cl:14][C:15]1[C:16]([CH3:24])=[N:17][C:18]([CH3:23])=[C:19]([Cl:22])[C:20]=1[S:21][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 13205564Methyl 5-chloro-4-nitrothiophene-2-carboxylateHCID 60207468Sodium 3,5-dichloro-2,6-dimethylpyridine-4-thiolate

Product 1

HCID 60207467Methyl 5-((3,5-dichloro-2,6-dimethylpyridin-4-yl)thio)-4-nitrothiophene-2-carboxylate

Procedure

Prepared according to the procedure described for example 18 from methyl 5-chloro-4-nitrothiophene-2-carboxylate (300 mg, 1.36 mmol) and sodium 3,5-dichloro-2,6-dimethylpyridine-4-thiolate (282 mg, 1.36 mmol) from above. The titled product was obtained as a solid (380 mg, 77% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.27 (1H, s), 3.83 (3H, s), 2.07 (3H, s), 2.05 (3H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2404b2ac3ec54ea6994977b8bc4e1d62
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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