Thionyl Chloride → HCID 14279665, compound

HRID 2291771Notes

Reaction equation

HRID 2291771 reaction equation
[C:1]([CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([N:16]3[C:24](=[O:25])[C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[C:17]3=[O:26])[C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:27])(=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]=[C:12]([N:16]3[C:17](=[O:26])[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=4[C:24]3=[O:25])[C:13]([F:15])=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:27])#[N:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 14347810HCID 14347810, compound

Product 1

HCID 14279665HCID 14279665, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

N,N-dimethylformamide (3 drops) was added to a mixture consisting of 2-[4-carbamoylmethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.2 g), toluene (30 ml) and thionyl chloride (0.2 g), and then the mixture was refluxed under heating for 3 hours. After the solvent was concentrated, toluene (50 ml) was added and fully mixed therewith, and then toluene was distilled off. The resulting solid was recrystalled from ethanol to give the desired 2-[4-cyanomethyl-7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.15 g). mp. 225°-229° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. concentrationAfter the solvent was concentrated
  4. additiontoluene (50 ml) was added
  5. additionfully mixed
  6. distillationtoluene was distilled off

Sources & evidence

ORD record
ord-6facb16927f34d51be7e96de3080bb5f
Source dataset
uspto-grants-1989_01
Patent number
US04798620

Reaction notes

Loading…