Pyridine → HCID 86735385, compound

HRID 1834220Notes

Reaction equation

HRID 1834220 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N[C:10]1[S:11][NH:12][C:13]2[CH:19]=[C:18]([O:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)(=[O:23])=[O:22])[CH:17]=[CH:16][C:14]=2[N:15]=1)(OC)=O.[C:34]([O:37][CH2:38]C)(=[O:36])C.[N:40]1C=CC=CC=1>O>[C:1]([N:12]1[C:13]2[CH:19]=[C:18]([O:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=3)(=[O:22])=[O:23])[CH:17]=[C:16]([NH2:40])[C:14]=2[N:15]=[C:10]([C:34]([O:37][CH3:38])=[O:36])[S:11]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 8857Ethyl AcetateHCID 21386599HCID 21386599, compound

Product 1

HCID 86735385HCID 86735385, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Milliliter of acetyl chloride was added dropwise, while stirring and cooling with an ice mixture, to a solution of 1.36 g of 3-carbomethoxyamino-7-(3-trifluoromethyl-phenylsulfonyloxy)-1H-2,1,4benzothiadiazine in 20 ml of pyridine. After the mixture had been stirred for 2 hours at 0° C, 1 ml of acetyl 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-Acetyl-3-carbomethoxy-amino-7-(3-trifluoromethyl-phenylsulfonyloxy)-1H-2,1,4-benzothiadiazine was obtained in a yield of 1.0 g.

Workup

  1. stirringAfter the mixture had 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-06901f1a17e74b018ad187f5cf921fb2
Source dataset
uspto-grants-1978_01
Patent number
US04069325

Reaction notes

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