2-Dimethylaminopyridine → HCID 15006005, compound

HRID 326533Notes

Reaction equation

HRID 326533 reaction equation
C[N:2]([C:4]1[CH:9]=CC=CN=1)C.[CH3:10][CH2:11][S:12]([C:14]1[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=1[C:16](C1NC=CC=1)=[O:17])=O>C1(C)C=CC=CC=1>[CH:4]1[N:2]2[C:11]([S:12][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]2=[O:17])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 218852-DimethylaminopyridineHCID 15272923HCID 15272923, compound

Product 1

HCID 15006005HCID 15006005, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dimethylaminopyridine (0.123 g, 1 mmol, 0.1 eq), 2-(2-ethylsulfinyl)benzoyl pyrrole (2.5 g, 10.1 mmol) and toluene (115 mL) are combined and refluxed with stirring in a flask covered with foil (to exclude light) for 29 hours, at which time the solvent is removed, in vacuo. The resulting crude solid is chromatographed to give 110 mg of comprising pyrrolo(2,1-b)-(1,3)benzothiazin-9-one (20 percent), 514 mg of pyrrolo(1,2-b)-(1,2)benzo-thiazin-10-one (46 percent) and 1.11 g of unreacted starting material. A small amount of 1H, 9H-(1)benzothiopyrano(3,2-b)pyrrol-9-one is detected by thin-layer chromatography but was not isolated. The pyrrolo(1,2-b)-(1,2)benzothiazin-10-one is recrystallized with EtOAc and hexanes to give an analytically pure yellow-orange solid (mp 100-102° C.).

Workup

  1. temperaturerefluxed
  2. customthe solvent is removed, in vacuo
  3. customThe resulting crude solid is chromatographed

Sources & evidence

ORD record
ord-681e9fc532ce4e21ab8472bd0d3c5c29
Source dataset
uspto-grants-1993_12
Patent number
US05270307

Reaction notes

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