Water → HCID 68819203, compound

HRID 1783615Notes

Reaction equation

HRID 1783615 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[C:12]3[S:16][C:15](=[S:17])[NH:14][C:13]3=[O:18])=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.IC.[CH:21](N(C(C)C)CC)(C)C.O>C(O)C>[CH3:21][S:17][C:15]1[S:16][C:12](=[CH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][N:3]=[CH:4]3)[C:13](=[O:18])[N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 76612360HCID 76612360, compound

Product 1

HCID 68819203HCID 68819203, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The suspension of 5-quinazolin-6-ylmethylene-2-thioxo-thiazolidin-4-one (example 1b, 2.6 g, 9.52 mmol), iodomethane (1.2 mL, 19.0 mmol) and diisopropylethylamine (DIEA) (2.4 mL, 14.3 mmol) in anhydrous ethanol (100 mL) was stirred at room temperature for 12 h. After adding water (200 mL), the solid was collected by filtration, washed with water and dried to obtain 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one (2.5 g, 92%) as a black solid. LC-MS m/e 288 (MH+).

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-bc890660d1544bbab5e2ef2deedd13b9
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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