Methanesulfonyl chloride → HCID 59313790, compound

HRID 889443Notes

Reaction equation

HRID 889443 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[C:5]#[N:6].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[C:5]([C:4]1[CH:3]=[C:2]([N:1]([S:14]([CH3:13])(=[O:16])=[O:15])[S:14]([CH3:13])(=[O:16])=[O:15])[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=1)#[N:6]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 112289743-Amino-5-nitrobenzonitrile

Product 1

HCID 59313790HCID 59313790, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-amino-5-nitrobenzonitrile (161 mg, 0.987 mmol) in DCM (8 mL) was added TEA (0.55 mL, 3.95 mmol), followed by methanesulfonyl chloride (0.165 mL, 2.12 mmol). The reaction mixture was stirred at room temperature for 60 min., then diluted with DCM, washed with H2O, dried over Na2SO4, and concentrated. The crude solid was triturated with DCM and isolated by filtration to give Intermediate 76A (242 mg, 76%) as a white solid. HPLC: Rt=1.198 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min, monitoring at 220 nm). 1H NMR (500 MHz, CDCl3) δ ppm 8.65 (1H, s), 8.45 (1H, s), 7.98 (1H, s), 3.48 (6H, s).

Workup

  1. washwashed with H2O
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude solid was triturated with DCM
  5. customisolated by filtration

Sources & evidence

ORD record
ord-1c3d07943fd5439fb4d38e297f230e3a
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

Loading…