Acetic Acid → HCID 23341984, compound

HRID 27748Notes

Reaction equation

HRID 27748 reaction equation
[O:1]=[C:2]1[NH:15][CH:14]=[C:5]2[S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[NH:9][C:4]2=[C:3]1[C:16]#[N:17].C(O)(=O)C.[Br:22]Br>C(Cl)(Cl)(Cl)Cl>[Br:22][C:12]1[CH:11]=[CH:10][C:8]2[NH:9][C:4]3[C:5](=[CH:14][NH:15][C:2](=[O:1])[C:3]=3[C:16]#[N:17])[S:6][C:7]=2[CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 125702342,3-dihydro-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile

Product 1

HCID 23341984HCID 23341984, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 20 parts of 2,3-dihydro-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile in 1575 parts of glacial acetic acid is added a solution of 34 parts of bromine in 320 parts of carbon tetrachloride. The resultant mixture is heated at the boiling point under reflux for 23/4 hours, then chilled. The precipitate which forms is filtered off and recrystallized from N,N-dimethylformamide to give 8-bromo-2,3-dihydro-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile melting above 305°.

Workup

  1. temperatureunder reflux for 23/4 hours
  2. temperaturechilled
  3. filtrationThe precipitate which forms is filtered off
  4. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-2b9648e8fd20486884ee7514cd49a739
Source dataset
uspto-grants-1980_09
Patent number
US04223136

Reaction notes

Loading…