Water → (2-chloro-4-pyrimidinyl)(3-methyl-1,3-benzothiazol-2(3H)-ylidene)ethanenitrile

HRID 854264Notes

Reaction equation

HRID 854264 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[N:14]=1)[C:11]#[N:12].[C:20]([O-])([O-])=O.[K+].[K+].CI.O>CS(C)=O>[Cl:19][C:15]1[N:14]=[C:13]([C:10](=[C:2]2[N:3]([CH3:20])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1]2)[C:11]#[N:12])[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 395229HCID 395229, compound

Product 1

HCID 72806198(2-chloro-4-pyrimidinyl)(3-methyl-1,3-benzothiazol-2(3H)-ylidene)ethanenitrileYield 5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1 (0.1 g, 0.35 mmol) in dry DMSO was added dry K2CO3 then methyl iodide and the suspension was shaken at rt. for 2 days. The precipitate formed by addition of water was filtered off then washed with water until neutral pH. The crude residue, dried under vacuum at 40° C., was triturated in warm acetonitrile, filtered off then dried under vacuum at 40° C., affording 5.6 mg (5%) of the title compound as a yellow powder.

Workup

  1. filtrationwas filtered off
  2. washthen washed with water until neutral pH
  3. dry with materialThe crude residue, dried under vacuum at 40° C.
  4. customwas triturated in warm acetonitrile
  5. filtrationfiltered off
  6. customthen dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-2c2c8c3e997646b4bb045e10cbeefc6e
Source dataset
uspto-grants-2007_08
Patent number
US07259162B2

Reaction notes

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