Dimethylformamide → 2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}-N-(5-methoxy-2-nitrophenyl)-N-methylacetamide

HRID 424867Notes

Reaction equation

HRID 424867 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:19]=[CH:18][C:12]([O:13][CH2:14][C:15]([OH:17])=O)=[CH:11][CH:10]=2)[S:3]1.S(Cl)(Cl)=O.CN(C)C=O.[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([N+:39]([O-:41])=[O:40])=[C:35]([NH:37][CH3:38])[CH:36]=1>C(#N)C.O>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]([N:37]([C:35]3[CH:36]=[C:31]([O:30][CH3:29])[CH:32]=[CH:33][C:34]=3[N+:39]([O-:41])=[O:40])[CH3:38])=[O:17])=[CH:18][CH:19]=2)[S:3]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 153056Benzenamine, 5-methoxy-N-methyl-2-nitro-HCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid

Product 1

HCID 116622722-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}-N-(5-methoxy-2-nitrophenyl)-N-methylacetamideYield 103%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
40 °C

Procedure

To a suspended solution of 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid (8.00 g) in acetonitrile (64 ml) were added thionyl chloride (3.38 g) and dimethylformamide (3.2 ml) at room temperature, and the resulting mixture was stirred successively at 25° C. for 30 minutes and at 40° C. for 30 minutes. Subsequently, to the reaction mixture were added successively N-(5-methoxy-2-nitrophenyl)-N-methylamine (3.84 g), N,N-dimethylaminopyridine (0.32 g) and acetonitrile (16 ml), and the resulting mixture was stirred at the same temperature for 1 hour. After cooling the reaction mixture to 0° C., water (32 ml) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (80 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate twice (16 ml for each) and evaporated to dryness to afford the title compound (9.67 g, yield: 100%) as an orange-colored amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  2. temperatureAfter cooling the reaction mixture to 0° C.
  3. extractionthe resulting mixture was extracted with ethyl acetate (80 ml)
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate twice (16 ml for each) and
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-23cb4580d5ef441a8c7d85d773368226
Source dataset
uspto-grants-2012_01
Patent number
US08106079B2

Reaction notes

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