Sodium Cyanide → 2-Hydroxybenzo[d]thiazole-5-carbonitrile

HRID 911576Notes

Reaction equation

HRID 911576 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[C-:12]#[N:13].[Na+]>CN1CCCC1=O.[Ni](Br)Br>[O:10]=[C:8]1[NH:7][C:6]2[CH:11]=[C:2]([C:12]#[N:13])[CH:3]=[CH:4][C:5]=2[S:9]1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 6038292(3H)-Benzothiazolone, 5-chloro-

Product 1

HCID 667070572-Hydroxybenzo[d]thiazole-5-carbonitrileYield 36.3%

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a mixture of 5-chloro-3H-benzothiazol-2-one (9.3 g, 50 mmol), nickel(II) bromide (10.9 g, 50 mmol) and sodium cyanide (4.91 g, 100 mmol) in 1-methyl-pyrrolidinone (100 mL) in a microwave reactor 5 to 200° C. over 15 min and hold 1 h. Filter the cooled mixture through a glass frit, add diethyl ether and brine and filter again. Wash the organic phase with brine three times and concentrate in vacuo. Pass the residue through a plug of silica gel eluting with hexane/EtOAc (2:1) and then dichloromethane/methanol (9:1) to obtain the desired intermediate (3.2 g, 36%). MS (ES+) m/z: 177 (M+H)+.

Workup

  1. temperatureHeat
  2. filtrationFilter the cooled mixture through a glass frit
  3. additionadd diethyl ether and brine
  4. filtrationfilter again
  5. washWash the organic phase with brine three times
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b97d45f65da845ba9deb55571d95fdd0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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