Toluene → HCID 14347815, compound

HRID 2291768Notes

Reaction equation

HRID 2291768 reaction equation
[C:1]([CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([N+:16]([O-:18])=[O:17])[C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:19])(=O)[NH2:2].S(Cl)(Cl)=O.C1(C)C=CC=CC=1>CN(C)C=O.CC(CC(C)C)=O>[C:1]([CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([N+:16]([O-:18])=[O:17])[C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:19])#[N:2]

Participants

6

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 14347809HCID 14347809, compound

Product 1

HCID 14347815HCID 14347815, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Two drops of N,N-dimethylformamide were added to a mixture of 4-carbamoylmethyl-7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (1.4 g), thionylchloride (1.2 g) and toluene (20 ml), and the mixture was stirred at a temperature of 100° C. to 110° C. for 6 hours. After the liquor was allowed to cool, methylisobutyl ketone (300 ml) was added thereto, and the liquor was washed with water, a saturated aqueous solution of sodium bicarbonate, water and a saturated table salt solution, in that order, subsequently dried with anhydrous sodium sulfate. After the solvent was distilled off, toluene (300 ml) and activated carbon (0.5 g) were added to the residue, the mixture was heated for a minute, and filtered while it was still hot. The resulting product was allowed to stand overnight, resulting crystals were recovered by filtration, and dried to give the desired 4-cyanomethyl-7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (0.64 g). When the residue obtained by distilling the mother liquor was recrystallized from a minimum amount of toluene, an additional amount (0.3 g) of the desired compound was produced. mp. 196°-200° C.

Workup

  1. temperatureto cool
  2. washthe liquor was washed with water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate, water and a saturated table salt solution, in that order, subsequently dried with anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. additiontoluene (300 ml) and activated carbon (0.5 g) were added to the residue
  6. temperaturethe mixture was heated for a minute
  7. filtrationfiltered while it
  8. waitto stand overnight
  9. customresulting crystals
  10. filtrationwere recovered by filtration
  11. customdried

Sources & evidence

ORD record
ord-fbc5ae3e15aa438c935a6dcbcb10148c
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

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