Triethylamine → HCID 21200467, compound

HRID 1601925Notes

Reaction equation

HRID 1601925 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 1 N 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 1 N 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-2b79d55c458649f4aa234b5d5f9e8a37
Source dataset
uspto-grants-1999_11
Patent number
US05977359

Reaction notes

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