Dimethylformamide dimethyl acetal → (E)-3-(dimethylamino)-1-(1-trityl-1H-imidazol-4-yl)prop-2-en-1-one

HRID 532900Notes

Reaction equation

HRID 532900 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25](=[O:27])[CH3:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][N:29]([CH:31](OC)OC)[CH3:30]>CO>[CH3:28][N:29]([CH3:31])/[CH:30]=[CH:26]/[C:25]([C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)=[O:27]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanone

Product 1

HCID 22273578(E)-3-(dimethylamino)-1-(1-trityl-1H-imidazol-4-yl)prop-2-en-1-oneYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(1-trityl-1H-imidazol-4-yl)ethanone (81.0 g, 230 mmol) and DMF-DMA (77.0 mL, 575 mmol) in MeOH (500 mL) was heated to reflux for 72 h. The mixture was then allowed to cool to RT and was then cooled to 0° C. the suspension was filtered and the filter cake was dried in vacuo at 40° C. to give the title compound (72.7 g) that was used as it is in the next step. UPLC-MS: MS 408.3 (M+H+); UPLC rt 1.08 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 72 h
  3. temperaturewas then cooled to 0° C. the suspension
  4. filtrationwas filtered
  5. customthe filter cake was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-76549268e76142b7bfeec39284a83526
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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