Benzoyl chloride → HCID 21386590, compound

HRID 1834222Notes

Reaction equation

HRID 1834222 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([NH:14][C:15]1[S:16](=[O:39])[NH:17][C:18]2[CH:24]=[C:23]([O:25][S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)(=[O:28])=[O:27])[CH:22]=[CH:21][C:19]=2[N:20]=1)([O:12][CH3:13])=[O:11].C(OCC)(=O)C>N1C=CC=CC=1.O>[C:1]([N:17]1[C:18]2[CH:24]=[C:23]([O:25][S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:36])[F:38])[CH:30]=3)(=[O:28])=[O:27])[CH:22]=[CH:21][C:19]=2[N:20]=[C:15]([NH:14][C:10]([O:12][CH3:13])=[O:11])[S:16]1=[O:39])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chloride2×HCID 8857Ethyl AcetateHCID 21386605HCID 21386605, compound

Product 1

HCID 21386590HCID 21386590, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

1 Milliliter of benzoyl chloride was added dropwise, while stirring and cooling with an ice mixture, to a solution of 1.4 g of 3-carbomethoxyamino-7-(3-trifluoromethyl-phenylsulfonyloxy)-1H-2,1,4-benzothiadiazine-S-oxide in 20 ml of pyridine. After the mixture has been stirred for 2 hours at 0° C, 1 ml of benzoyl chloride was added once more. After another hour of stirring at 0° C, the reaction mixture was diluted with water. It was then shaken with ethyl acetate, and the extract was washed with saturated sodium chloride solution. After evaporation of the solvent, the residue was isolated by trituration with methanol and filtration. 1-Benzoyl-3-carbomethoxyamino-7-(3-trifluoromethyl-phenylsulfonyloxy)-1H-2,1,4-benzothiadiazine-S-oxide was obtained in a yield of 1.1 g.

Workup

  1. stirringAfter the mixture has been stirred for 2 hours at 0° C
  2. stirringAfter another hour of stirring at 0° C
  3. washthe extract was washed with saturated sodium chloride solution
  4. customAfter evaporation of the solvent
  5. customthe residue was isolated by trituration with methanol and filtration

Sources & evidence

ORD record
ord-53ea3389edf8404ab79a97511399af25
Source dataset
uspto-grants-1978_01
Patent number
US04069325

Reaction notes

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