1,3-Dibromopropane → 2-(3-bromopropyl)-7-methoxy-1,2,4-benzothiadiazin-3(4H)one 1,1-dioxide

HRID 620059Notes

Reaction equation

HRID 620059 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[NH:7][C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[H-].[Na+].[Na].[Br:19][CH2:20][CH2:21][CH2:22]Br>CN(C=O)C>[Br:19][CH2:20][CH2:21][CH2:22][N:9]1[C:8](=[O:13])[NH:7][C:6]2[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[S:10]1(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 5360545SodiumHCID 125284907-Methoxy-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 190234312-(3-bromopropyl)-7-methoxy-1,2,4-benzothiadiazin-3(4H)one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.03 mol of 7-methoxy-1,2,4-benzothiadiazin-3(4H)one 1,1-dioxide is dissolved in 50 ml of absolute DMF, and 0.03 mol of sodium hydride is added. After 15 minutes, formation of the sodium salt was complete. The 0.06 mol of 1,3-dibromopropane is added dropwise and the mixture is heated at 80° C. for 2 hours. The solvent is then distilled out and the residue is purified by column chromatography on silica gel. The eluting agent used was a mixture of CH2Cl2 /CH3OH (98:2).

Workup

  1. distillationThe solvent is then distilled out
  2. customthe residue is purified by column chromatography on silica gel
  3. additiona mixture of CH2Cl2 /CH3OH (98:2)

Sources & evidence

ORD record
ord-2897115ebd4d4550a586a68ea4b6662a
Source dataset
uspto-grants-1989_04
Patent number
US04818756

Reaction notes

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