Dimethyl Sulfoxide → 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-oxo-acetamide

HRID 992445Notes

Reaction equation

HRID 992445 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([OH:39])[C:20]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]#[C:34][CH2:35][CH3:36])=[C:27]([O:37][CH3:38])[CH:26]=2)=[O:21])[CH:15]=[CH:16][C:17]=1[Cl:18].C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[CH:13]=[C:14]([C:19](=[O:39])[C:20]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]#[C:34][CH2:35][CH3:36])=[C:27]([O:37][CH3:38])[CH:26]=2)=[O:21])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 184057672-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-acetamide

Product 1

HCID 184057762-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-oxo-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 0.8 ml oxalyl chloride (9.0 mmol) in 8 ml methylenchloride at −63° C. is added in 15 minutes a solution of 0.84 ml DMSO (12.0 mmol) in 4 ml CH2Cl2. A solution of 2.6 g (6.0 mmol) of 2-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-acetamide in 30 ml CH2Cl2 is added during 10 minutes. After 10 minutes at −65° C. a solution of 3.2 ml (24.0 mmol) triethylamine in 8 ml CH2Cl2 is added during 15 minutes. After another 15 minutes at the same temperature the mixture is hydrolysed with 6.0 ml water and allowed to warm up to room temperature. The solution is washed with solutions of KHSO4 (20%), NaHCO3 (saturated) and NaCl (saturated) After evaporation the residue is submitted to flash-chromatography (ethyl acetate 25, hexanes 75) to give the 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-oxo-acetamide.

Workup

  1. washThe solution is washed with solutions of KHSO4 (20%), NaHCO3 (saturated) and NaCl (saturated)
  2. customAfter evaporation the residue

Sources & evidence

ORD record
ord-a30880c345dc43e3a7da23ce712de556
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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