Dimethylformamide → HCID 54227172, compound

HRID 224610Notes

Reaction equation

HRID 224610 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:14])(=[O:13])[N:5]([CH3:15])[C:4]=1[C:16]([OH:18])=O.S(Cl)([Cl:21])=O.CN(C)C=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:14])(=[O:13])[N:5]([CH3:15])[C:4]=1[C:16]([Cl:21])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 3692738HCID 3692738, compound

Product 1

HCID 54227172HCID 54227172, compoundYield 21,801.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.2 gm (23 millimols) of 4-methoxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid-1,1-dioxide were suspended in 60 ml of benzene and 8.2 ml (0.11 millimols) of thionyl chloride and 0.5 ml of anhydrous dimethylformamide were added to the suspension. The reaction mixture was refluxed for 6 hours, stirred overnight at room temperature and evaporated in vacuo. The residue was dissolved in a little toluene, and the solution was evaporated, yielding 6.9 gm (100% of theory) of 4-methoxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid chloride-1,1-dioxide.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in a little toluene
  4. customthe solution was evaporated

Sources & evidence

ORD record
ord-ee301fb5c9304fe3a9e998d975edd71f
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

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