Acetic Acid → HCID 18694064, compound

HRID 1603715Notes

Reaction equation

HRID 1603715 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[NH4+:5].[C:6]([CH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH:15]([N:22]1[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29]C=3C(OCC)=O)[N:24]=[C:23]1[C:38](OCC)=[O:39])[C:16]2=O)([O:8][CH2:9][CH3:10])=[O:7].[C:43](O)(=O)[CH3:44]>C(Cl)Cl>[C:1]([C:2]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:25]1[N:24]=[C:23]2[C:38](=[O:39])[NH:5][C:16]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:12]([CH2:11][C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:13]=4[CH2:14][C:15]=3[N:22]2[CH:26]=1)([O:4][CH2:43][CH3:44])=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 18694043HCID 18694043, compound

Product 1

HCID 18694064HCID 18694064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.07 g of ammonium acetate are added to a solution of 2.15 g of ethyl 1-(4-carbethoxymethyl-1-oxoindan-2-yl)-4-(2-carbethoxyphenyl)imidazole-2-carboxylate in 25 ml of acetic acid and the mixture is stirred for 4 hours 30 minutes at boiling temperature and then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 50° C. The product obtained is dissolved in 100 ml of methylene chloride and the solution is washed 3 times with a total of 150 ml of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 50° C. The product obtained is washed 4 times with a total of 200 ml of ethyl ether and dried under reduced pressure (0.5 mm Hg; 0.07 kPa) at 60° C. 1.4 g of ethyl 2-(2-carbethoxyphenyl)-4-oxo-4,5-dihydro-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-9-acetate are thus obtained in the form of a grey powder which decomposes without melting above 260° C. [1H NMR spectrum in DMSO-d6, T=300K, δ in ppm (250 MHz): 1.15 (3H, t, J=6 Hz, CH3), 1.25 (3H, t, J=6 Hz, CH3), 3.87 (2H, s, CH2CO), 4.00 (2H, s, CH2), 4.15 (2H, q, J=6 Hz, OCH2), 4.27 (2H, q, J=6 Hz, OCH2), 7.25 (1H, d, J=7 Hz, arom. CH), 7.42 and 7.50 (1H each, t, J=7 Hz, 2 arom. CH), 7.65 (2H, m, 2 arom. CH), 7.85 (2H, m, 2 arom. CH), 8.30 (1H, s, imidazole CH), 12.50 (1H, s, NHCO)].

Workup

  1. concentrationconcentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 50° C
  2. customThe product obtained
  3. washthe solution is washed 3 times with a total of 150 ml of distilled water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 50° C
  6. customThe product obtained
  7. washis washed 4 times with a total of 200 ml of ethyl ether
  8. customdried under reduced pressure (0.5 mm Hg; 0.07 kPa) at 60° C

Sources & evidence

ORD record
ord-84bbff2f885643e680f58d1feadad11a
Source dataset
uspto-grants-1999_11
Patent number
US05990108

Reaction notes

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