Dimethylformamide dimethyl acetal → ethyl 4-[(E)-dimethylaminomethylideneamino]-1H-imidazole-5-carboxylate

HRID 1875245Notes

Reaction equation

HRID 1875245 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12][N:13]([CH:15](OC)OC)[CH3:14]>CN(C=O)C>[CH3:12][N:13](/[CH:15]=[N:1]/[C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:14]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 343359ethyl 4-amino-1H-imidazole-5-carboxylate

Product 1

HCID 87550540ethyl 4-[(E)-dimethylaminomethylideneamino]-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 4-amino-1H-imidazole-5-carboxylate (0.65 g, 4.19 mmol) and DMF-DMA (11.22 ml, 84 mmol) in DMF (3 mL) was stirred at RT under nitrogen for 3 days. The excess DMF-DMA and DMF were removed under vacuum to give the desired compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.34-13.68 (m, 1H), 8.09 (s, 1H), 7.36 (s, 1H), 4.12 (q, 2H), 2.96 (d, 6H), 1.22 (t, 3H).

Workup

  1. customThe excess DMF-DMA and DMF were removed under vacuum

Sources & evidence

ORD record
ord-c0c21aef5cae47b6ad62cf3e3ff2700d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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