Triethylamine → 3-Amino-2-Benzyl-5-Methoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

HRID 1252027Notes

Reaction equation

HRID 1252027 reaction equation
[CH2:1]([NH:8][S:9](Cl)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([NH:17][C:18](=[NH:21])[O:19][CH3:20])(OC)=O.C([N:24](CC)CC)C>C1COCC1>[NH2:24][C:13]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:9](=[O:11])(=[O:10])[N:21]=[C:18]([O:19][CH3:20])[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13529095Benzylsulfamyl chlorideHCID 137319931Methyl N-(iminomethoxymethyl)carbamate

Product 1

HCID 201409183-Amino-2-Benzyl-5-Methoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzylsulfamoyl chloride (168 g) in anhydrous THF (300 ml) is added dropwise to a stirred solution of N-carbomethoxy-O-methylisourea (107 g) and triethylamine (90 g) in anhydrous THF (800 ml) under nitrogen at -70° C. The resulting suspension is warmed to RT, filtered and the filtrate evaporated in vacuo. The residue is partitioned between methylene chloride and 0.5N aqueous HCl. The organic layer is dried, filtered, and concentrated in vacuo affording the desired product as an oil.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated in vacuo
  3. customThe residue is partitioned between methylene chloride and 0.5N aqueous HCl
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62b52b96d75b476896011517204416ba
Source dataset
uspto-grants-1988_05
Patent number
US04742055

Reaction notes

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