Dimethyl Sulfoxide → HCID 59321452, compound

HRID 1800824Notes

Reaction equation

HRID 1800824 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].Cl[CH2:13][CH2:14][N:15]([CH2:23][CH2:24]Cl)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].CS(C)=O>C(OCC)(=O)C>[C:10]([C:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[CH2:24][CH2:23][N:15]([C:16]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:22])[CH2:14][CH2:13]1)#[N:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 19660Carbonate IonHCID 229020Benzeneacetonitrile, 2,3-dichloro-HCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 59321452HCID 59321452, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(2,3-dichlorophenyl)acetonitrile (2.49 g crude, est. 83% purity, 11 mmol), 2.70 g tert-butyl bis(2-chloroethyl)carbamate (J. Med. Chem. 1992, 35, 11, 2033-2039) (11 mmol), 19.5 g aesium carbonate (60 mmol) and 200 ml DMSO were combined in a round bottom flask and stirred at room temperature for 4 days. The reaction mixture was diluted with ethyl acetate and the organic layer washed with 1M aq. KHSO4 solution, and then saturated aq. NaHCO3 solution, then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The product was purified by column chromatography on silica, using a gradient from 5% to 35% ethyl acetate in hexanes as eluent. 2.3 g of the title compound were isolated as an oil (59% yield)

Workup

  1. washthe organic layer washed with 1M aq. KHSO4 solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-ca44cc99ca3346389606882531aa7c25
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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