Triethylamine → HCID 21200467, compound

HRID 1957077Notes

Reaction equation

HRID 1957077 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([N:15]1[CH2:20][CH2:19][O:18][C:17]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=2)([CH2:21][CH2:22][OH:23])[CH2:16]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[C:7]([N:15]1[CH2:20][CH2:19][O:18][C:17]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=2)([CH2:21][CH:22]=[O:23])[CH2:16]1)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11416728HCID 11416728, compound

Product 1

HCID 21200467HCID 21200467, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A solution of 0.32 ml of oxalyl chloride in 7.3 ml of DCM is cooled to -78° C. under a nitrogen atmosphere and a solution of 0.51 ml of DMSO in 3.5 ml of DCM is added dropwise, followed by a solution of 1 g of the compound obtained in step A of EXAMPLE 27 in 7.5 ml of DCM and 0.7 ml of DMSO. The reaction mixture is stirred for 30 minutes at -60° C., 2 ml of triethylamine are then added and the reaction mixture is stirred while the temperature is allowed to rise to RT. It is washed with 1N HCl solution, with saturated Na2CO3 solution and with water, the organic phase is dried over MgSO4 and the solvent is evaporated off under vacuum to give 1.03 g of the expected product in the form of an oil.

Workup

  1. stirringthe reaction mixture is stirred while the temperature
  2. customto rise to RT
  3. washIt is washed with 1N HCl solution, with saturated Na2CO3 solution and with water
  4. dry with materialthe organic phase is dried over MgSO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-75c951c9169447b39cfac82f0fe1d7fd
Source dataset
uspto-grants-1998_07
Patent number
US05780466

Reaction notes

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