Dimethylformamide → HCID 66937462, compound

HRID 538146Notes

Reaction equation

HRID 538146 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[CH:6][C:5]([NH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[C:24]1([CH2:30][SH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCOC(C)=O>[CH2:30]([S:31][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([N+:10]([O-:12])=[O:11])=[C:5]([NH2:9])[CH:6]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 66937462HCID 66937462, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 4,5-dichloro-2-nitro-phenylamine (3.00 g, 14.5 mmol) and DMF (72 mL) was added K2CO3 (5.31 g, 29.0 mmol) and phenyl-methanethiol (3.94 g, 31.7 mmol). The mixture was heated to 70° C. for 18 h and then cooled to 23° C. The reaction mixture was dissolved in EtOAc (200 mL), washed with saturated sodium bicarbonate solution (100 mL), washed with brine (3×100 mL). The organic layers were combined, dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (5-45% EtOAc/hexanes) to yield the titled compound (2.39 g, 56%). MS (ESI/CI): mass calcd. for C13H11ClN2O2S, 294.0; m/z found, 295.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 7.96 (s, 1H), 7.56 (s, 2H), 7.50 (d, J=7.2 Hz, 2H), 7.37 (t, J=7.5 Hz, 2H), 7.31 (t, J=7.4 Hz, 1H), 7.05 (s, 1H), 4.27 (s, 2H).

Workup

  1. temperaturecooled to 23° C
  2. washwashed with saturated sodium bicarbonate solution (100 mL)
  3. washwashed with brine (3×100 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified (FCC) (5-45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d6644c54aa204ceda6f6572336092e67
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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