Dimethyl Sulfoxide → HCID 19036656, compound

HRID 264342Notes

Reaction equation

HRID 264342 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:15][CH:14]=1)#[N:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])=[CH:15][CH:14]=1)#[N:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19036671HCID 19036671, compound

Product 1

HCID 19036656HCID 19036656, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

A solution of DMSO (9.36 g, 120 mmol) in 20 mL of CH2Cl2 was added dropwise over 10 minutes to a solution of oxalyl chloride (10.16 g, 80 mmol) in CH2Cl2 (80 mL) at -70° C. under an atmosphere of nitrogen. After stirring for 15 minutes at -70° C., a solution of the product of step B (7.56 g, 40.0 mmol) in CH2Cl2 (50 mL) was added dropwise over 10 minutes and the solution was stirred at -70° C. for 15 minutes. Neat triethylamine (24.2 g, 240 mmol) was added rapidly, the ice bath was removed and the mixture allowed to warm to ambient temperature over 30 minutes. The reaction mixture was diluted with CH2Cl2 (100 mL), washed successively with water, 1N NaHSO4 and brine, dried (MgSO4), filtered through a pad of silica gel and eluted with CH2C2. The solvent was evaporated under reduced pressure affording 7.23 g of title product (97%) as a thick oil of sufficient purity to be used in the next reaction. 1H-NMR (300 MHz, CDCl3) δ1.67 (m, 4H), 2.47 (m, 2H), 2.70 (m, 2H), 7.37 (d, J=8 HZ, 2H), 7.48 (d, J=8 Hz, 2H), 9.77 (s, 1H).

Workup

  1. stirringthe solution was stirred at -70° C. for 15 minutes
  2. customthe ice bath was removed
  3. temperatureto warm to ambient temperature over 30 minutes
  4. additionThe reaction mixture was diluted with CH2Cl2 (100 mL)
  5. washwashed successively with water, 1N NaHSO4 and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a pad of silica gel
  8. washeluted with CH2C2
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ebeaf11acdc04da6ba6c90a306d24516
Source dataset
uspto-grants-1997_07
Patent number
US05646183

Reaction notes

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