Dimethylformamide → HCID 66937535, compound

HRID 538138Notes

Reaction equation

HRID 538138 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[Cl:9][C:10]1[C:15](Cl)=[CH:14][C:13]([NH2:17])=[C:12]([N+:18]([O-:20])=[O:19])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O>[Cl:9][C:10]1[C:15]([S:8][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=2)=[CH:14][C:13]([NH2:17])=[C:12]([N+:18]([O-:20])=[O:19])[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79303-ThiocresolHCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 66937535HCID 66937535, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-methyl-benzenethiol (2.30 mL, 19.3 mmol), 4,5-dichloro-2-nitro-phenylamine (2.00 g, 9.66 mmol), potassium carbonate (2.67 g, 19.3 mmol), and DMF (48 mL) was heated at 90° C. for 16 h. The reaction mixture was cooled to 23° C. EtOAc was added and the organic layer was washed with saturated aqueous NaHCO3 (2×80 mL) and brine (1×80 mL). The aqueous layers were extracted with EtOAc (3×80 mL). The organic layers were combined, dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (0-100% EtOAc/hexanes) to yield the titled compound (2.30 g, 81%). 1H NMR (400 MHz, CDCl3): 8.12 (s, 1H), 7.41-7.36 (m, 3H), 7.34-7.30 (m, 1H), 5.95 (s, 1H), 5.88 (br s, 2H), 2.41 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to 23° C
  2. washthe organic layer was washed with saturated aqueous NaHCO3 (2×80 mL) and brine (1×80 mL)
  3. extractionThe aqueous layers were extracted with EtOAc (3×80 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified (FCC) (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b0f6b60bdbb54204992fefa766ea924d
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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