Thionyl Chloride → HCID 14347816, compound

HRID 2291770Notes

Reaction equation

HRID 2291770 reaction equation
[C:1]([CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16])(=O)[NH2:2].S(Cl)(Cl)=O>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16])#[N:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 14347808HCID 14347808, compound

Product 1

HCID 14347816HCID 14347816, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-carbamoylmethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (2.24 g), toluene (20 ml), thionyl chloride (2.4 g) and N,N-dimethylformamide (3 drops) was stirred at a temperature of 90° C. to 100° C. for 2 hours. The solvent was distilled off from the mixture, and then methylisobutyl ketone (100 ml) was added thereto and the resulting mixed solution was filtered, the filtrate was washed with water, sodiumbicarbonate solution, and water, in that order, and subsequently dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give the desired 4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-one (1.74 g). mp. 111°-113° C.

Workup

  1. distillationThe solvent was distilled off from the mixture
  2. additionmethylisobutyl ketone (100 ml) was added
  3. additionthe resulting mixed solution
  4. filtrationwas filtered
  5. washthe filtrate was washed with water, sodiumbicarbonate solution, and water, in that order
  6. dry with materialsubsequently dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1e08dbbe78b642c0b9632ab5c357545f
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

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