O-mesitylenesulfonylhydroxylamine → HCID 178425981, compound

HRID 64996Notes

Reaction equation

HRID 64996 reaction equation
[NH2:1][C:2]1[NH:3][SH:4](=[O:19])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.[C:20]1([CH3:33])[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28]([NH:31]O)(=[O:30])=[O:29]>ClCCl>[C:20]1([CH3:33])[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28]([OH:19])(=[O:30])=[O:29].[NH2:1][C:2]1[N:7]([NH2:31])[C:6]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:5]=2[SH:4](=[O:19])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

4

Reactant 2

HCID 11009332O-mesitylenesulfonylhydroxylamineHCID 178508179HCID 178508179, compound

Product 1

HCID 178425981HCID 178425981, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 18.2 g of 3-amino-7-chloro-1-phenyl-1,2,4-benzothiadiazine-1-oxide in 75 ml dichloromethane is added slowly a solution of 16.1 g mesitylene sulfonylhydroxylamine (MSH) in 90 ml dichloromethane at 0° C. under stirring. Thereafter stirring is continued for one hour at room temperature and the precipitate then sucked off, washed with diethylether and air-dried. Colorless 3,4-diamino-7-chloro-1-phenyl-1,2,4-benzothiadiazine-1-oxide mesitylene sulfonate, m. pt. 225° C., are obtained. To 10.0 g thereof, suspended in 30 ml pyridine are added under stirring 8.3 g trifluoroacetic acid anhydride. After four hours of boiling the solvent is distilled in a water-jet pump vacuum. The residue is partitioned in dichloromethane/aqueous sodium bicarbonate. The organic layer is concentrated and the residue recrystallized from ethanol. A 3.9 g colorless solid product is obtained, m. pt. 167° C.

Workup

  1. stirringThereafter stirring
  2. washwashed with diethylether
  3. customair-dried

Sources & evidence

ORD record
ord-df2051de13a14466abd26800e8b8883d
Source dataset
uspto-grants-1986_09
Patent number
US04612311

Reaction notes

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