Dimethylformamide → HCID 13051488, compound

HRID 223775Notes

Reaction equation

HRID 223775 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:22])[NH:10][CH:11]=[C:12]3[C:17]=2[NH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13]3)=[CH:4][CH:3]=1.[CH3:23][N:24](C=O)C>O>[C:23]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:22])[NH:10][CH:11]=[C:12]3[C:17]=2[NH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13]3)=[CH:4][CH:3]=1)#[N:24]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 13051487HCID 13051487, compound

Product 1

HCID 13051488HCID 13051488, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 parts of 4-(4-bromophenyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one suspended in 300 parts of DMF is added 4 parts of cuprous cyanide and the reaction mixture is refluxed for 2 to 12 hours. After cooling, water is added and the solution extracted with ethyl acetate. The combined extracts are washed with saturated NaCl solution and dried. Solvent removal gives a residue which upon recrystallization from aqueous DMF gives 4-(4-cyanophenyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one, which melts above 290° C.

Workup

  1. temperaturethe reaction mixture is refluxed for 2 to 12 hours
  2. temperatureAfter cooling
  3. extractionthe solution extracted with ethyl acetate
  4. washThe combined extracts are washed with saturated NaCl solution
  5. customdried
  6. customSolvent removal
  7. customgives a residue which
  8. customupon recrystallization from aqueous DMF

Sources & evidence

ORD record
ord-c48e18d341f64a3bbde65f5d8e335f97
Source dataset
uspto-grants-1982_10
Patent number
US04356302

Reaction notes

Loading…