Hydrochloric Acid → HCID 18800685, compound

HRID 849139Notes

Reaction equation

HRID 849139 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[OH:24].C(N(CC)CC)C.Cl>C(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=[O:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18800751HCID 18800751, compound

Product 1

HCID 18800685HCID 18800685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Neat, dry DMSO (4 equivalents) is added slowly to a CH2Cl2 solution of the oxalyl chloride (1.25 equivalents) cooled to -70° C. under N2. After stirring for about 15 min., the product of Example 193 (1 equivalent) in CH2Cl2 is added slowly. Neat triethylamine (4 equivalents) is then added and the mixture is warmed to 0° C. After 30 min., the mixture is poured into stirred ice-water and neutralized with dilute HCl. The mixture is then separated and the aqueous layer extracted with CH2Cl2. The organic extracts are then combined, washed with dilute brine, dried (MgSO4) and stripped of all solvent under reduced pressure. The crude title compound is purified by column chromatography.

Workup

  1. temperaturethe mixture is warmed to 0° C
  2. waitAfter 30 min.
  3. additionthe mixture is poured
  4. customThe mixture is then separated
  5. extractionthe aqueous layer extracted with CH2Cl2
  6. washwashed with dilute brine
  7. dry with materialdried (MgSO4)
  8. customThe crude title compound is purified by column chromatography

Sources & evidence

ORD record
ord-32b0ae1527a545bb9c0de559672bc9d8
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

Loading…