O-Xylene → N-(6-fluoro-2-pyridyl)-3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

HRID 354621Notes

Reaction equation

HRID 354621 reaction equation
[CH3:1][N:2]1[CH:7]([C:8]([O:10]C)=O)[C:6](=[O:12])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[S:3]1(=[O:18])=[O:17].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[N:21]=1.C1(C)C(C)=CC=CC=1>CO>[F:26][C:22]1[N:21]=[C:20]([NH:19][C:8]([CH:7]2[C:6](=[O:12])[C:5]3[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=3[S:3](=[O:18])(=[O:17])[N:2]2[CH3:1])=[O:10])[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 120152Methyl 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxideHCID 27613996-Fluoropyridin-2-amine

Product 1

HCID 15917676N-(6-fluoro-2-pyridyl)-3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxideYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture consisting of 7.68 g (0.0285 mole) of methyl 3,4-dihydro-2-methyl-4-oxo-2H-benzothiazine-3-carboxylate 1,1-dioxide, 4.8 g (0.0428 mole) of 2-amino-6-fluoropyridine, and 29 ml of xylene was refluxed for 17 hours, during which the methanol formed by this reaction was continuously distilled off. After the mixture was cooled by allowing it to stand overnight, the resulting precipitate was separated by filtration. The filtrate was concentrated and then cooled to obtain an additional precipitate, which was combined with the previously obtained precipitate and washed with hot chloroform. Thus, 7.2 g of crystals having a melting point of 246°-248° C. (decomp.) were obtained in a 72.3% yield.

Workup

  1. customformed by this reaction
  2. distillationwas continuously distilled off
  3. temperatureAfter the mixture was cooled
  4. customthe resulting precipitate was separated by filtration
  5. concentrationThe filtrate was concentrated
  6. temperaturecooled
  7. customto obtain an additional precipitate, which
  8. washwashed with hot chloroform
  9. customwere obtained in a 72.3% yield

Sources & evidence

ORD record
ord-347b5b82cb4b4a0888065abf0ef50b4c
Source dataset
uspto-grants-1983_03
Patent number
US04376119

Reaction notes

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