Dimethyl Sulfoxide → HCID 57638156, compound

HRID 2111482Notes

Reaction equation

HRID 2111482 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:33]=[CH:32][C:21]([O:22][CH2:23][C:24]3[CH:31]=[CH:30][C:27]([CH2:28][OH:29])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][N:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:33]=[CH:32][C:21]([O:22][CH2:23][C:24]3[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57637965HCID 57637965, compound

Product 1

HCID 57638156HCID 57638156, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of DMSO (2.6 equivalents) in dry DCM, cooled to −78° C. under N2 was added oxalyl chloride (1.1 equivalents) in DCM drop-wise. The solution was stirred at −78° C. for 5 minutes before a solution of 4-[4-(4-methylpiperazin-1-yl)phenoxymethyl]benzyl alcohol (1 equivalent) in DCM was added drop-wise, and allowed to stir at −78° C. for another 30 minutes. Triethylamine (2.5 equivalents) was slowly dripped in before allowing the solution to reach ambient temperatures. The solution was washed with aqueous NaHCO3 and brine, dried over MgSO4 and concentrated to provide the crude 4-[4-(4-methylpiperazin-1-yl)phenoxymethyl]benzaldehyde which was converted to thiosemicarbazones according to Scheme 2.

Workup

  1. additionwas added drop-wise
  2. washThe solution was washed with aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf5b1a46e63a4c02b1ff15750adff61a
Source dataset
uspto-grants-2009_04
Patent number
US07521062B2

Reaction notes

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