Ammonia → 2-(2,3-Dihydro-2-ethyl-4-oxo-4H-1-benzopyran-6-yl)propionamide

HRID 26684Notes

Reaction equation

HRID 26684 reaction equation
[CH2:1]([CH:3]1[CH2:8][C:7](=[O:9])[C:6]2[CH:10]=[C:11]([CH:14]([CH3:18])[C:15](O)=[O:16])[CH:12]=[CH:13][C:5]=2[O:4]1)[CH3:2].C([N:21](CC)CC)C.ClC(OCC)=O.N.Cl>O1CCCC1>[CH2:1]([CH:3]1[CH2:8][C:7](=[O:9])[C:6]2[CH:10]=[C:11]([CH:14]([CH3:18])[C:15]([NH2:21])=[O:16])[CH:12]=[CH:13][C:5]=2[O:4]1)[CH3:2]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 127698112-(2,3-dihydro-2-ethyl-4-oxo-4H-1-benzopyran-6-yl)propionic acid

Product 1

HCID 127698172-(2,3-Dihydro-2-ethyl-4-oxo-4H-1-benzopyran-6-yl)propionamideYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(2,3-dihydro-2-ethyl-4-oxo-4H-1-benzopyran-6-yl)propionic acid (10.0 g; 0.04 mol) in dry tetrahydrofuran (100 ml) at -20° C. was added triethylamine (4.05 g; 0.04 mol) followed by ethyl chloroformate (6.0 g; 0.056 mol). After 10 minutes the mixture was saturated with gaseous ammonia. It was then acidified with dilute hydrochloric acid, the organic solvent was removed in vacuo and the product was extracted with chloroform (4×80 ml). The combined extracts were washed with water (2×100 ml), brine (200 ml), and dried over MgSO4. Evaporation of the solvent and recrystallisation of the residue from ethyl acetate gave the title compound (wt=5.1 g). m.p. 148°-150° C.

Workup

  1. customthe organic solvent was removed in vacuo
  2. extractionthe product was extracted with chloroform (4×80 ml)
  3. washThe combined extracts were washed with water (2×100 ml), brine (200 ml)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent and recrystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-5f3098aa15074039ab97f8a650219173
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Reaction notes

Loading…