Dabco → HCID 4640412, compound

HRID 341174Notes

Reaction equation

HRID 341174 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C1N2CCN(CC2)C1.[CH3:15][N:16]([CH3:21])[S:17](Cl)(=[O:19])=[O:18]>CC#N>[CH3:15][N:16]([CH3:21])[S:17]([N:4]1[CH:3]=[C:2]([Br:1])[CH:6]=[N:5]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 9237DabcoHCID 163754-BromopyrazoleHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 4640412HCID 4640412, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromopyrazole (2.20 g, 15 mmol) and DABCO (1.85 g, 16.5 mmol) in anhydrous MeCN (15 ml) at room temperature was added dimethylsulfamoyl chloride (1.61 ml, 15 mmol). The reaction mixture was stirred for 20 h, then partitioned between 1N HCl(aq) and EtOAc. The aqueous layer was extracted with EtOAc (×2), the organics combined, washed with brine (×1), dried (MgSO4), filtered and the solvent removed in vacuo to afford a colourless liquid. (3.79 g). 1H NMR (400 MHz, CDCl3): 8.00 (1H, s), 7.70 (1H, s), 2.99 (6H, s).

Workup

  1. custompartitioned between 1N HCl(aq) and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc (×2)
  3. washwashed with brine (×1)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto afford a colourless liquid

Sources & evidence

ORD record
ord-a91904b6c4854fbdba0ca0916bfc1aa0
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

Loading…