Dimethylformamide → Methyl 2-((3-methyl-4-nitroisothiazol-5-yl)carbamoyl)benzoate

HRID 1850698Notes

Reaction equation

HRID 1850698 reaction equation
Br[C:2]1[S:6][N:5]=[C:4]([CH3:7])[C:3]=1[N+:8]([O-:10])=[O:9].[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[K].CN([CH:26]=[O:27])C>>[CH3:7][C:4]1[C:3]([N+:8]([O-:10])=[O:9])=[C:2]([NH:13][C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:12]([O:27][CH3:26])=[O:11])=[O:21])[S:6][N:5]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 2740915-Bromo-3-methyl-4-nitro-1,2-thiazoleHCID 178515024HCID 178515024, compound

Product 1

HCID 90411396Methyl 2-((3-methyl-4-nitroisothiazol-5-yl)carbamoyl)benzoate

Procedure

A mixture of 5-bromo-3-methyl-4-nitro-isothiazole (200 mg, 0.8967 mmol), (1,3-dioxoisoindolin-2-yl)potassium (174.4 mg, 0.9415 mmol) in dry DMF (2 mL) was stirred at RT overnight. The mixture was quenched by the addition of methanol, stirred at RT for 1 h, then the reaction mixture was concentrated in vacuo. The residue was triturated in a small volume of dry MeOH. The precipitate was collected by filtration and dried in vacuo, yielding methyl 2-((3-methyl-4-nitroisothiazol-5-yl)carbamoyl)benzoate as a pale yellow solid. (165 mg, 57%) MS (ES+) 322.1.

Workup

  1. customThe mixture was quenched by the addition of methanol
  2. stirringstirred at RT for 1 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe residue was triturated in a small volume of dry MeOH
  5. filtrationThe precipitate was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5db088bc2f48436eb4f04f77bd008f95
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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