Triethylamine → N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-4-chlorophenoxyacetamide

HRID 1904225Notes

Reaction equation

HRID 1904225 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][N:16]1[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]1[CH3:22].C(N(CC)CC)C.CP(OP(CC)(C)=O)(CC)=O>CN(C)C=O>[CH3:22][C:17]1[N:16]([CH2:15][CH2:14][NH:13][C:8](=[O:10])[CH2:7][O:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=2)[C:20]([CH3:21])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 26229(4-Chlorophenoxy)acetic acidHCID 103894Phosphinic acid, P-ethyl-P-methyl-, P,P'-anhydrideHCID 13770050HCID 13770050, compound

Product 1

HCID 13770057N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-4-chlorophenoxyacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.3 g (0.05 mol) of 4-chlorophenoxyacetic acid, 6.9 g (0.05 mol) of 1-(2-aminoethyl)-2,5-dimethylpyrrole and 35 ml of triethylamine are dissolved in 50 ml of dimethylformamide. At -5° to 0° C., 20 ml of methylethylphosphinic anhydride are added dropwise, and the mixture is then stirred at room temperature for 3 h. The reaction mixture is poured into ice-cold aqueous sodium bicarbonate solution, and the mixture is extracted with methylene chloride and the extract is concentrated. The residue is chromatographed over a 20 cm silica gel column using a 1:1 methylene chloride/ethyl acetate mixture as the mobile phase, and the product is crystallized using ligroin. Yield: 10.5 g (69% of theory), Melting point: 75°-77° C. Elemental analysis: C16H19CLN2O2 (306.80) calculated: C 62.6 H 6.2 CL 11.6 N 9.1 0 10.4 found: C 62.7 H 6.4 CL 11.7 N 9.2 0 10.4

Workup

  1. additionThe reaction mixture is poured into ice-cold aqueous sodium bicarbonate solution
  2. extractionthe mixture is extracted with methylene chloride
  3. concentrationthe extract is concentrated
  4. customThe residue is chromatographed over a 20 cm silica gel column
  5. customthe product is crystallized

Sources & evidence

ORD record
ord-606d326a18894badb83cf9795ed4e838
Source dataset
uspto-grants-1989_06
Patent number
US04837225

Reaction notes

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