Water → (5Z)-2-(methylthio)-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one

HRID 2053294Notes

Reaction equation

HRID 2053294 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>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][CH:3]=[CH:4]3)/[C:13](=[O:18])[N:14]=1

Participants

6

Reactant 4

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

Product 1

HCID 58585737(5Z)-2-(methylthio)-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The suspension of 5-[1-quinolin-6-yl-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one (10.2 g, 37.5 mmol), iodomethane (4.65 mL, 75 mmol) and DIEA (N,N-diisopropylethylamine) (9.8 mL, 56.3 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-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one (8.76 g, 82%) as a grey solid. LC-MS m/e 287 (MH+).

Workup

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

Sources & evidence

ORD record
ord-9f8b64884a1242a58ced3f02142fa893
Source dataset
uspto-grants-2008_02
Patent number
US07326786B2

Reaction notes

Loading…