Acetic Acid → HCID 18694035, compound

HRID 1870812Notes

Reaction equation

HRID 1870812 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]C(C(OCC)=O)=[CH:29][CH:28]=3)[N:24]=[C:23]1[C:38]([O:40]CC)=O)[C:16]2=O)([O:8][CH2:9][CH3:10])=[O:7].[C:43](O)(=O)[CH3:44]>>[C:1]([C:2]1[CH:31]=[CH:32][C:27]([C:25]2[N:24]=[C:23]3[C:38](=[O:40])[NH:5][C:16]4[C:17]5[CH:18]=[CH:19][CH:20]=[C:12]([CH2:11][C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:13]=5[CH2:14][C:15]=4[N:22]3[CH:26]=2)=[CH:28][CH:29]=1)([O:4][CH2:43][CH3:44])=[O:3]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium Acetate2×HCID 18694037HCID 18694037, compound

Product 1

HCID 18694035HCID 18694035, compound

Conditions

Temperature
60 °C

Procedure

4.38 g of ammonium acetate are added to a solution of 2.9 g of ethyl 1-(4-carbethoxymethyl-1-oxoindan-2-yl)-4-(4-carbethoxyphenyl)imidazole-2-carboxylate in 25 ml of acetic acid and the mixture is stirred for 2 hours at boiling temperature and again for 2 hours after addition of 1 g of ammonium acetate. After cooling to 60° C., the insoluble matter is separated by filtration, washed 3 times with a total of 45 ml of acetic acid, 3 times with a total of 90 ml of ethyl ether and dried under reduced pressure (0.5 mm Hg; 0.07 kPa) at 60° C. 1.8 g of ethyl 2-(4-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 beige solid which decomposes without melting above 260° C. [1H NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 1.20 (3H, t, J=6 Hz, CH3), 1.35 (3H, t, J=6 Hz, CH3), 3.85 (2H, s, CH2CO), 4.00 (2H, s, CH2), 4.12 (2H, q, J=6 Hz, OCH2), 4.35 (2H, q, J=6 Hz, OCH2), 7.25 (1H, d, J=7 Hz, arom. CH), 7.40 (1H, t, J=7 Hz, arom. CH), 7.85 (1H, d, J=7 Hz, arom. CH), 8.05 and 8.15 (2H each, d, J=7 Hz, PhCO2H.), 8.70 (1H, s, imidazole CH), 12.10 (1H, s, NHCO)].

Workup

  1. customthe insoluble matter is separated by filtration
  2. washwashed 3 times with a total of 45 ml of acetic acid, 3 times with a total of 90 ml of ethyl ether
  3. customdried under reduced pressure (0.5 mm Hg; 0.07 kPa) at 60° C

Sources & evidence

ORD record
ord-adc32cbb0a1a4ca4abf96cc17aa15a61
Source dataset
uspto-grants-2000_08
Patent number
US06100264

Reaction notes

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