Methyl iodide → HCID 136351323, compound

HRID 2393381Notes

Reaction equation

HRID 2393381 reaction equation
[Na].[OH:2][N:3]=[C:4]1[C:16]2[N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13](=[O:20])[NH:12][C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2.[CH3:21]I.[Cl-].[NH4+]>N.O.C(O)C>[CH3:21][O:2][N:3]=[C:4]1[C:16]2[N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13](=[O:20])[NH:12][C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 178518650HCID 178518650, compound

Product 1

HCID 136351323HCID 136351323, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.1 g of sodium is dissolved in 3 ml of liquid ammonia at -33° C., followed by portionwise addition of 0.3 g of 10-hydroxyimino-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one. After stirring for 30 minutes, 0.3 g of methyl iodide is added dropwise and the stirring is continued for 4 hours at the same temperature and then for 16 hours while allowing the temperature to return gradually to 20° C. The solid obtained is suspended in a solution of 0.25 g of ammonium chloride in 20 ml of distilled water and, after stirring for 15 minutes, it is filtered and washed with distilled water. The solid obtained is suspended in 50 ml of boiling ethanol, filtered at 20° C., washed twice with 10 ml in total of ethyl ether and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.2 g of 10-methoxyimino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained as a 95/5 mixture of the E and Z forms, subliming at 310° C. (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 4.22 (s, 3H: =NOCH3); 7.37 and 7.50 (2 broad t, J=8 Hz, 1H each: --H 7 and --H 8); 7.57 and 8.01 (2s, 1H each: --H of the imidazole); 7.76 and 8.00 (2 broad d, J=8 Hz, 1H each: --H 6 and --H 9); from 12.50 to 13.00 (broad mult., 1H: --CONH--)).

Workup

  1. waitthe stirring is continued for 4 hours at the same temperature
  2. waitfor 16 hours while allowing
  3. customto return gradually to 20° C
  4. customThe solid obtained
  5. stirringafter stirring for 15 minutes
  6. filtrationit is filtered
  7. washwashed with distilled water
  8. customThe solid obtained
  9. filtrationfiltered at 20° C.
  10. washwashed twice with 10 ml in total of ethyl ether
  11. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-99a2feddbeac4825938232b18abc7786
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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