Sodium Carbonate → HCID 21273257, compound

HRID 1382786Notes

Reaction equation

HRID 1382786 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH:26]=O.[C:28]([C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)(=[O:30])[CH3:29].[OH-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH3:1][C:2]1[N:6]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=[N:4][C:3]=1/[CH:26]=[CH:29]/[C:28]([C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:30]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 128023-AcetylindoleHCID 14797Potassium HydroxideHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 21273257HCID 21273257, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-methyl-1-(triphenylmethyl)-1H-imidazol-4-carboxaldehyde (4.90 g), 3-acetylindole (2.24 g) and potassium hydroxide (6.08 g) in absolute ethanol (100 ml) and water (50 ml) was heated at 80° for 24 h. The suspension was poured into 2N sodium carbonate solution (300 ml) and extracted with dichloromethane (3×150 ml). The combined extracts were dried, filtered and evaporated to give an orange solid (6.5 g) which was triturated with ethyl acetate (50 ml) to give the title compound (2.42 g) as a yellow solid, m.p. 240°-242°.

Workup

  1. temperaturewas heated at 80° for 24 h
  2. extractionextracted with dichloromethane (3×150 ml)
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4290af1a2af44dc0afb7619f4b8da515
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

Loading…