Ethanol → 5-(4-Ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one

HRID 853019Notes

Reaction equation

HRID 853019 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7](/[CH:11]=[C:12]3/[C:13](=[O:18])[NH:14][C:15](=[S:17])[S:16]/3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.IC.[CH:21](N(CC)C(C)C)(C)C.O.[CH2:31]([OH:33])[CH3:32]>>[CH2:31]([O:33][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([CH:11]=[C:12]3[S:16][C:15]([S:17][CH3:21])=[N:14][C:13]3=[O:18])[CH:6]=2)[N:1]=[CH:2][CH:3]=1)[CH3:32]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 116662315-[1-Quinolin-6-yl-meth-(z)-ylidene]-2-thioxo-thiazolidin-4-one

Product 1

HCID 694667775-(4-Ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-oneYield 84%

Procedure

To the suspension of 5-[1-quinolin-6-yl-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one (example 40a) (2.4 g, 20 mmol), iodomethane (2.54 mL, 40 mmol) and DIEA (N,N-diisopropylethylamine) (6.4 mL, 30 mmol) in anhydrous ethanol (70 mL) was stirred at room temperature for 24 h. After adding water (50 mL), the solid was collected by filtration, washed with water and dried to give 5-(4-ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one (5.67 g, 84%) as a yellow solid. LC-MS m/e 331 (MH+)

Workup

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

Sources & evidence

ORD record
ord-1cdc1aa425d14a22907e76068842379c
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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