Cesium carbonate → (4-nitrophenyl) (NZ)-N-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]carbamate

HRID 924279Notes

Reaction equation

HRID 924279 reaction equation
[NH:1]=[C:2]1[N:6]([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=2[CH:14]([CH3:16])[CH3:15])[C:5](=[O:17])[CH2:4][S:3]1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.ClCCl>[CH:14]([C:8]1[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=1[N:6]1[C:5](=[O:17])[CH2:4][S:3]/[C:2]/1=[N:1]\[C:19](=[O:20])[O:21][C:22]1[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=1)([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 821294-Nitrophenyl chloroformateHCID 904041312-Imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one

Product 1

HCID 117622068(4-nitrophenyl) (NZ)-N-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]carbamateYield 86.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A round-bottomed flask was charged with 2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (CA49) (1.30 g, 5.23 mmol), 4-Nitrophenyl chloroformate (1.06 g, 5.23 mmol) and cesium carbonate (1.71 g, 5.23 mmol) were dissolved in acetonitrile (13 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The reaction was diluted with dichloromethane and adsorbed onto silica gel. Purification by flash column chromatography using 0-100% ethyl acetate/hexanes as eluent provided the title compound as a dark red solid (1.88 g, 86%): 1H NMR (400 MHz, CDCl3) δ 8.31-8.18 (m, 2H), 7.39-7.27 (m, 4H), 6.92-6.83 (m, 1H), 4.14-4.00 (m, 2H), 2.61 (p, J=6.9 Hz, 1H), 2.36 (d, J=0.7 Hz, 3H), 1.30-1.10 (m, 6H); ESIMS m/z 414 ([M+H]+).

Workup

  1. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-15312c7d0e2c4ba383d8a77eb075d404
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

Loading…