Thionyl Chloride → 3-(N,N-Dimethylsulfamoyl)-4-methoxybenzyl chloride

HRID 901194Notes

Reaction equation

HRID 901194 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:9]O)(=[O:5])=[O:4].S(Cl)([Cl:19])=O>C(Cl)Cl>[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:9][Cl:19])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 657511993-(N,N-Dimethylsulfamoyl)-4-methoxybenzyl alcohol

Product 1

HCID 219768673-(N,N-Dimethylsulfamoyl)-4-methoxybenzyl chlorideYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of OBS02053 (2.33 g, 8.89 mmol) in anhydrous DCM (50 mL) was added thionyl chloride (0.97 mL, 13.34 mmol). The mixture was stirred at room temperature for 2 h and the volatiles removed in vacuo. The residue was re-dissolved and co-evaporated three times with DCM (3×20 mL) to give OBS02058 as a light-sensitive brown oil (2.07 g, 83%); 1H-NMR (270 MHz, CDCl3)=2.98 (6H, s), 3.89 (3H, s), 4.54 (2H, s), 6.94 (1H, d, J=8.4), 7.25 (1H, dd, J=2.2, 8.4), 7.40 (1H, d, J=2.2).

Workup

  1. customthe volatiles removed in vacuo
  2. dissolutionThe residue was re-dissolved

Sources & evidence

ORD record
ord-36fd3da7199a4a2b8b7c77120472a4e9
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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