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

HRID 1017812Notes

Reaction equation

HRID 1017812 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-acetamideYield 77%

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 in 10 minutes. After 10 minutes at −65° C. a solution of 3.2 ml (24.0 mmol) triethylamine in 8 ml CH2Cl2 is added in 15 minutes. After 15 more minutes at that temperature the mixture is hydrolysed with 6.0 ml water and warmed up to +20° C. The solution is washed with solutions of KHSO4 (20%), saturated NaHCO3 and saturated NaCl. After evaporation the residue is submitted to flash-chromatography (ethyl acetate 25, hexanes 75) to give 2.0 g (77%) of the 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-oxo-acetamide. 1H-NMR (300 MHz, CDCl3): 1.15 (t, 3 H, CH2CH3), 2.22 (m, 2 H, CH2CH3), 2.87 (t, 2 H, CH2CH2), 3.64 (t, 2 H, CH2CH2), 3.88 (s, 3 H, OCH3), 4.72 (m, 2 H, OCH2), 6.77 (m, 2 H, CH arom.), 6.99 (d, 1 H, CH arom.), 7.16 (t, 1 H, NH), 7.57 (d, 8.22, m) and 8.49 (m, 3 H, CH arom.).

Workup

  1. temperaturewarmed up to +20° C
  2. washThe solution is washed with solutions of KHSO4 (20%), saturated NaHCO3 and saturated NaCl
  3. customAfter evaporation the residue

Sources & evidence

ORD record
ord-83a01acfe56643afa5de860d8562a099
Source dataset
uspto-grants-2002_11
Patent number
US06479550B1

Reaction notes

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