Methyl iodide → Thiazolo(5,4-c)isoquinolin-5(4H)-one, 2,4-dimethyl-

HRID 224341Notes

Reaction equation

HRID 224341 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[NH:5][C:6](=[O:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH3:1][C:2]1[S:3][C:4]2[N:5]([CH3:18])[C:6](=[O:15])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 23332770HCID 23332770, compound

Product 1

HCID 3057676Thiazolo(5,4-c)isoquinolin-5(4H)-one, 2,4-dimethyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6.48 g. (0.030 mole) of 2-methyl-thiazolo[5,4-c]isoquinoline-5(4H)-one in 64 ml of dimethylformamide was added with 1.45 g of a 50% (by weight) suspension of sodium hydride in mineral oil (0.030 mole of sodium hydride). The resulting mixture was kept at 60° C. for 2 hours and, after cooling to room temperature, was added with 2.37 ml (0.038 mole) of methyl iodide and heated for 1 hour at 60° C. After evaporating the solvent, the residue was taken up with water and the obtained solid was collected, washed with water, dried and finally crystallized from methylene chloride/methanol. Yield 4.5 (65%) of the title compound. M.p. 174-176. The compound is the N-isomer.

Workup

  1. additionA suspension of 6.48 g
  2. temperatureheated for 1 hour at 60° C
  3. customAfter evaporating the solvent
  4. customthe obtained solid was collected
  5. washwashed with water
  6. customdried
  7. customfinally crystallized from methylene chloride/methanol

Sources & evidence

ORD record
ord-bd71303dd22c41d9be9a1c1bb0ad4442
Source dataset
uspto-grants-1980_11
Patent number
US04232017

Reaction notes

Loading…