Riluzole → HCID 68485467, compound

HRID 1966058Notes

Reaction equation

HRID 1966058 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.ClC[C:18]#[N:19]>[OH-].[Na+].C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:10][C:4]=1[S:3][CH2:2][C:18]#[N:19]

Participants

6

Reactant 2

HCID 5070RiluzoleHCID 7856Chloroacetonitrile

Product 1

HCID 68485467HCID 68485467, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 2-amino-6-trifluoromethoxybenzothiazole (1.8 g, 7.7 mmol) in 10 N NaOH (30 ml) is refluxed, under a current of nitrogen, for 2 hours, after which time the suspension becomes a clear solution, and to which chloroacetonitrile (0.48 ml, 7.7 mmol) in CH2Cl2 (50 ml) and tetrabutylammonium hydrogensulphate (0.26 g, 0.77 mmol) are added. The resulting reaction mixture is stirred for 18 hours at room temperature, then the organic phase is separated, washed with water and dried over Na2SO4. The solvent is evaporated and the residue chromatographed through silica, eluting with petroleum ether/AcOEt (1:1) to give the product as a dark oil (1.1 g, 58% yield). 1H-NMR (CDCl3): 3.45 (s, 2H), 4.44 (br s, 2H), 6.74 (d, J=8.8, 1H), 7.10 (m, 1H), 7.39 (m, 1H). MS (ESI): m/z 249 (M+H+).

Workup

  1. temperatureis refluxed
  2. customThe resulting reaction mixture
  3. customthe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customThe solvent is evaporated
  7. customthe residue chromatographed through silica
  8. washeluting with petroleum ether/AcOEt (1:1)

Sources & evidence

ORD record
ord-b6010fb68f064c5b8ecb7c4da7eae447
Source dataset
uspto-grants-2013_04
Patent number
US08420634B2

Reaction notes

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