Carbon Tetrachloride → HCID 23341995, compound

HRID 27750Notes

Reaction equation

HRID 27750 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C.C(Cl)(Cl)(Cl)Cl.[N+:28]([C:31]1[CH:48]=[CH:47][C:34]2[NH:35][C:36]3[C:37](=[CH:40][NH:41][C:42](=[O:46])[C:43]=3[C:44]#[N:45])[S:38](=O)[C:33]=2[CH:32]=1)([O-:30])=[O:29]>CN(C)C=O>[N+:28]([C:31]1[CH:48]=[CH:47][C:34]2[NH:35][C:36]3[C:37](=[CH:40][NH:41][C:42](=[O:46])[C:43]=3[C:44]#[N:45])[S:38][C:33]=2[CH:32]=1)([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 233419942,3-dihydro-8-nitro-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile 10-oxide

Product 1

HCID 23341995HCID 23341995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 27 parts of triphenylphosphine in a mixture of 195 parts of acetonitrile with 400 parts of carbon tetrachloride is added 12 parts of a 1:1 solvate of 2,3-dihydro-8-nitro-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile 10-oxide with N,N-dimethylformamide. The resultant mixture is heated at the boiling point under reflux with stirring for 15 minutes, then chilled. The precipitate which forms is isolated by filtration and recrystallized from a mixture of N,N-dimethylformamide and methanol to give 2,3-dihydro-8-nitro-3-oxo-5H-pyrido[3,4-b][1,4]benzothiazine-4-carbonitrile solvated 2:1 with N,N-dimethylformamide which melts above 305°. The solvent of crystallization can be removed by heating at around 200° in vacuo.

Workup

  1. temperatureunder reflux
  2. temperaturechilled
  3. customThe precipitate which forms is isolated by filtration
  4. customrecrystallized from a mixture of N,N-dimethylformamide and methanol

Sources & evidence

ORD record
ord-32d6677f5e334d3c9a9fba612a077df8
Source dataset
uspto-grants-1980_09
Patent number
US04223136

Reaction notes

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