Thionyl Chloride → HCID 21976878, compound

HRID 11891Notes

Reaction equation

HRID 11891 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[CH2:5]O.S(Cl)([Cl:18])=O>C(Cl)Cl.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[CH2:5][Cl:18]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 657510183-Bromo4-(N,N-dimethylsulfamoyl)benzyl alcohol

Product 1

HCID 21976878HCID 21976878, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of OBS02002 (5.0 g, 16.12 mmol) in anhydrous DCM (50 mL) was added thionyl chloride (1.76 mL, 24.18 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 a yellow oil which solidified on standing. The solid was stirred in n-hexane, filtered and air-dried to give OBS02003 as an off-white solid (5.01 g, 95%). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.79; 1H-NMR (270 MHz, CDCl3)=3.05 (6H, s), 4.51 (2H, s), 7.32 (1H, dd, J=2.2, 8.4), 7.48 (1H, d, J=8.4), 7.62 (1H, d, J=2.2). Dimethylsulfamic Acid 2-bromo-4-{[(4-cyano-phenyl)-[1,2,4]triazol-4-ylamino]methyl}phenyl ester (OBS02005, STX732)

Workup

  1. customthe volatiles removed in vacuo
  2. dissolutionThe residue was re-dissolved
  3. customco-evaporated three times with DCM (3×20 mL) to give a yellow oil which
  4. filtrationfiltered
  5. customair-dried

Sources & evidence

ORD record
ord-a7100408e04744a39debe8e7490bc02b
Source dataset
uspto-grants-2006_08
Patent number
US07098343B2

Reaction notes

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