Triethylamine → HCID 21282817, compound

HRID 2050238Notes

Reaction equation

HRID 2050238 reaction equation
[N:1]#[C:2]Br.[Cl:4][C:5]1[C:14]2[NH:13][S:12](=[O:16])(=[O:15])[N:11]([CH:17]([CH3:19])[CH3:18])[C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C>ClCCCl>[Cl:4][C:5]1[C:14]2[N:13]([C:2]#[N:1])[S:12](=[O:16])(=[O:15])[N:11]([CH:17]([CH3:18])[CH3:19])[C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 136318848-Chloro-2,2-dioxo-3-propan-2-yl-1H-2lambda6,1,3-benzothiadiazin-4-one

Product 1

HCID 21282817HCID 21282817, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

127 parts of cyanogen bromide are added to 274.5 parts of 8-chloro-3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide dissolved in 1,500 parts of 1,2-dichloroethane at 5°-10° C. and 121 parts of triethylamine are then added dropwise at the same temperature. The reaction mixture is then stirred for 48 hours at room temperature (20° C.), after which it is washed twice with water and three times with normal aqueous sodium hydroxide solution and dried, and the solvent is evaporated off under reduced pressure. The residue is recrystallized twice from isopropanol and gives 90 parts of 8-chloro-1-cyano-3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide of melting point 123°-124° C.

Workup

  1. washafter which it is washed twice with water and three times with normal aqueous sodium hydroxide solution
  2. customdried
  3. customthe solvent is evaporated off under reduced pressure
  4. customThe residue is recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-e61a9d307f4344b98cde5e6fca4ad106
Source dataset
uspto-grants-1980_04
Patent number
US04200743

Reaction notes

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