Benzyl Bromide → 4-(N-benzyl-N-(furan-2-ylmethyl)sulfamoyl)benzoic acid

HRID 548034

Reaction equation

HRID 548034 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][S:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)(=[O:10])=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:27]([N:7]([CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[S:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 6815254-[(Furan-2-ylmethyl)sulfamoyl]benzoic acid

Product 1

HCID 241346434-(N-benzyl-N-(furan-2-ylmethyl)sulfamoyl)benzoic acidYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
165 °C

Procedure

4-(N-(furan-2-ylmethyl)sulfamoyl)benzoic acid (Example 5-2b) (140 mg, 0.5 mmol) and Cesium Carbonate (325 mg, 1 mmol) were placed in a microwave vial and dissolved in 2 mL DMF. (Bromomethyl)benzene (170 mg, 1 mmol) was added into the reaction mixture. The reaction was placed in a microwave reactor and heated at 165° C. for 5 minutes. The reaction mixture was dissolved in Ethyl Acetate and washed with water. The organic layer was dried over sodium sulfate and evaporated under vacuum. The crude product was dissolved in 4/1 solution of 6N NaOH (aq)/tetrahydrofuran (3 mL) and stirred at ambient temperature for 6 hours. The solution was acidified with 3N HCl (aq) to a pH of ˜3 and the product was extracted with ethyl acetate (3×, 75 mL). The combined organic extracts were dried over sodium sulfate and concentrated under vacuum. The residue was taken up in methanol (3 mL) and purified by reverse phased HPLC (5-95% acetonitrile in H2O gradient:25 minutes). Yield 35%. MS M+H calculated 372.4, found 372.0.

Workup

  1. customThe reaction was placed in a microwave reactor
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under vacuum
  5. dissolutionThe crude product was dissolved in 4/1 solution of 6N NaOH (aq)/tetrahydrofuran (3 mL)
  6. extractionthe product was extracted with ethyl acetate (3×, 75 mL)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. custompurified by reverse
  10. customHPLC (5-95% acetonitrile in H2O gradient:25 minutes)

Sources & evidence

ORD record
ord-085209d24d7e4fd3a75fcdd0a12291a0
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Linked notes

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