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

HRID 2108171Notes

Reaction equation

HRID 2108171 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. Then 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 CH2Cl2CH3OH (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 CH2Cl2CH3OH (98:2)

Sources & evidence

ORD record
ord-2cd402c551ec410bb8fa8a7c54541322
Source dataset
uspto-grants-1990_06
Patent number
US04937343

Reaction notes

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