Triethylamine → 3-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methylimidazolidine-2,4-dione

HRID 1638928

Reaction equation

HRID 1638928 reaction equation
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[C:19]2[O:18][CH:17]([CH3:20])[CH2:16][C:15]=2[C:14]([N:21]=[C:22]=[O:23])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:10][C:11]1[C:19]2[O:18][CH:17]([CH3:20])[CH2:16][C:15]=2[C:14]([N:21]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:22]2=[O:23])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 537184027-Chloro-2,3-dihydro-4-isocyanato-2-methylbenzofuran

Product 1

HCID 679267013-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methylimidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.30 g of sarcosine ethyl ester hydrochloride was added over 5 minutes to a mixture of 2.10 g of 34A, 1.52 g of triethylamine and 60 mL of methylene chloride, under nitrogen at 25°-30° C. The mixture was stirred at room temperature for 24 hours, then diluted with 100 mL of methylene chloride, washed with water, then brine, dried (MgSO4) and stripped of solvent. The residue was dissolved in 70 mL of a 1:1 v:v mixture of ethanol and 2N hydrochloric acid. The solution was refluxed for 4 hours, the resulting mixture was stirred at room temperature overnight, stripped of volatiles, diluted with water and extracted with methylene chloride. The extract was dried (MgSO4) and stripped of solvent. The residue was purified by flash chromatography over silica gel with a 1:2 v:v mixture of hexane and ethyl acetate as eluent to give the title compound, as a glass/sticky solid.

Workup

  1. washwashed with water
  2. dry with materialbrine, dried (MgSO4)
  3. dissolutionThe residue was dissolved in 70 mL of a 1:1 v
  4. additionv mixture of ethanol and 2N hydrochloric acid
  5. temperatureThe solution was refluxed for 4 hours
  6. stirringthe resulting mixture was stirred at room temperature overnight
  7. additiondiluted with water
  8. extractionextracted with methylene chloride
  9. dry with materialThe extract was dried (MgSO4)
  10. customThe residue was purified by flash chromatography over silica gel with a 1:2 v
  11. additionv mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-bd9a27dcc7714ef98eaa6eb0f4f951db
Source dataset
uspto-grants-1989_11
Patent number
US04881967

Linked notes

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