Dimethyl Sulfoxide → HCID 4941244, compound

HRID 1753762Notes

Reaction equation

HRID 1753762 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].CS(C)=O>CC(C)=O>[C:5]([NH:3][C:2]([NH:14][C:13]1[CH:15]=[CH:16][C:10]([CH3:9])=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1)=[S:1])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6367Acetyl chlorideHCID 83904-Methyl-3-nitroanilineHCID 15666Ammonium thiocyanate

Product 1

HCID 4941244HCID 4941244, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of ammonium thiocyanate (1.05 g, 13.85 mmol) in acetone (21 mL) was added dropwise acetyl chloride (0.90 mL 12.70 mmol). The reaction mixture was stirred at 40° C. for 30 min. Then, a solution of 4-methyl-3-nitroaniline (1.76 g, 11.54 mmol) in acetone (7 mL) was added and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was poured into ice-water and the precipitate was filtered, washed with more water and cyclohexane to give compound IV-c as brown solid in 50% yield. (300 MHz, DMSO) δ 12.45 (s, 1H), 11.53 (s, 1H), 8.38 (d, J=2.0 Hz, 1H), 7.69 (dd, J=8.3, 2.0 Hz, 1H), 7.43 (d, J=8.3 Hz, 1H), 2.44 (s, 3H), 2.09 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 4 h
  2. filtrationthe precipitate was filtered
  3. washwashed with more water and cyclohexane
  4. customto give compound IV-c as brown solid in 50% yield

Sources & evidence

ORD record
ord-c67a8e534f244d0b95dfc4fb4a6cd2e3
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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