Ethyl chloroformate → HCID 178527221, compound

HRID 64998Notes

Reaction equation

HRID 64998 reaction equation
[NH2:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:6]=2[SH:5](=[O:19])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:4][C:3]1=[NH:20].[H-].[Na+].Cl[C:24](OCC)=[O:25]>O1CCCC1>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]2[N:2]3[NH:1][C:24]([OH:25])=[N:20][C:3]3=[N:4][SH:5](=[O:19])([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 178509314HCID 178509314, compound

Product 1

HCID 178527221HCID 178527221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7.0 g of 4-amino-7-chloro-3,4-dihydro-3-imino-1-phenyl-1,2,4-benzothiadiazine-1-oxide, prepared according to Example 6, in 250 ml tetrahydrofurane are added 0.68 g of sodium hydride (80%) in portions. After stirring for 30 minutes at room temperature 2.4 ml ethyl chloroformate, dissolved in 10 ml tetrahydrofuran, are added dropwise. The mixture is stirred at room temperature for three hours, then separated from the precipitated sodium chloride and concentrated. The residue is dissolved in 150 ml toluene and boiled for 16 hours under reflux. The precipitated product is sucked off and crystallized from dimethylformamide/methanol as colorless crystals, m. pt. 343°-348° C.

Workup

  1. additionare added dropwise
  2. customseparated from the precipitated sodium chloride
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in 150 ml toluene
  5. waitboiled for 16 hours
  6. temperatureunder reflux
  7. customcrystallized from dimethylformamide/methanol as colorless crystals, m. pt. 343°-348° C.

Sources & evidence

ORD record
ord-25f0743f0b0a43f7998a41c47665422a
Source dataset
uspto-grants-1986_09
Patent number
US04612311

Reaction notes

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