1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → HCID 42635546, compound

HRID 1972136Notes

Reaction equation

HRID 1972136 reaction equation
[C:1]1(=[O:17])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[CH:2]1[C:11]1C=CN=C[CH:12]=1.[C:18]([N:37]1C=C(C=O)[N:39]=[CH:38]1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:18]([N:37]1[CH:12]=[C:11]([CH:2]2[C:1](=[O:17])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:10])[N:39]=[CH:38]1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 694901HCID 694901, compound

Product 1

HCID 42635546HCID 42635546, compoundYield 67%

Procedure

The condensing of commercially available 1-trityl-1H-imidazole-4-carboxaldehyde (I) with phtalide to form 2-(1-trityl-1H-imidazole-4-yl)indan-1,3-dione (II) is performed under the conditions that are similar to those used for synthesis of 4-(indane-1,3-dionyl)pyridine J. Org. Chem. 1971, vol. 36, p. 1563. surprisingly, the bulky 1-trityl-1H-imidazole-4-carboxaldehyde (I) reacted as expected and produced 2-(1-trityl-1H-imidazole-4-yl)indan-1,3-dione (II) in over 67% yield. Both ethyl acetate and dioxane can be used as reaction media.

Sources & evidence

ORD record
ord-e4fdd5e23a5b418c82829c465e7583c9
Source dataset
uspto-grants-2013_04
Patent number
US08431717B2

Reaction notes

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