1,4-Dibromobutane → 1-(4-Bromobutyl)-3-(4-chlorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818772Notes

Reaction equation

HRID 1818772 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][S:15]2(=[O:24])=[O:23])=[CH:10][CH:9]=1.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>CN(C=O)C.C(OCC)C>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([C:11]2[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=2)[S:15]1(=[O:23])=[O:24]

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 10796Cesium carbonateHCID 57886358HCID 57886358, compound

Product 1

HCID 578862331-(4-Bromobutyl)-3-(4-chlorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 59%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (0.29 g, 0.9 mmol) was added to a solution of 1-(4-chlorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (Made analogously as in general procedure I, 0.25 g, 0.9 mmol), and 1,4-dibromobutane (0.42 mL, 3.6 mmol) in dry DMF (5.0 mL) under nitrogen. After 3 h, the reaction mixture was diluted with diethyl ether and washed with water and brine. The ether layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give 0.41 g of crude product. The crude product was pre-adsorbed onto Celite and purified via Isco chromatography (Redisep, silica, gradient 5-30% ethyl acetate in hexane) to afford 0.22 g (59%) of 1-(4-bromobutyl)-3-(4-chlorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide.

Workup

  1. washwashed with water and brine
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give 0.41 g of crude product
  6. custompurified via Isco chromatography (Redisep, silica, gradient 5-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3f6b6fd63d5a4566b768f598d28cce5b
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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