Sodium hydride → 4-Bromo-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 1180626Notes

Reaction equation

HRID 1180626 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.[CH3:9][N:10]([CH3:15])[S:11](Cl)(=[O:13])=[O:12]>O1CCCC1.[Cl-].[NH4+]>[CH3:9][N:10]([CH3:15])[S:11]([N:7]1[CH:8]=[C:4]([Br:3])[N:5]=[CH:6]1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 178418934HCID 178418934, compound

Product 1

HCID 221479874-Bromo-N,N-dimethyl-1H-imidazole-1-sulfonamideYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Sodium hydride (55% in oil, 0.31 g) was added to a stirred solution of 4-bromo-1H imidazole (1.02 g) in dry tetrahydrofuran (20 mL) at room temperature under N2. After 10 minutes, dimethylsulfamoyl chloride (0.81 mL) was added. After stirring for 5 hours, the mixture was diluted with saturated aqueous ammonium chloride (20 mL) and extracted with ethyl acetate (20 mL). The extract was dried over Na2SO4, filtered and concentrated. The white solid was rinsed with diethyl ether and dried to give 1-(dimethylaminosulfonyl)-4-bromoimidazole (1.53 g, 87%). MS (ES+) 256, 254 ([MH]+). Step 2: 1-(Dimethylaminosulfonyl)-4-(4-fluorophenyl)imidazole

Workup

  1. extractionextracted with ethyl acetate (20 mL)
  2. dry with materialThe extract was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe white solid was rinsed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-b750ecc6ac3f443ba9a0587299c49ef0
Source dataset
uspto-grants-2007_10
Patent number
US07282513B2

Reaction notes

Loading…