Cyclopropanecarbonyl chloride → HCID 22713464, compound

HRID 351852Notes

Reaction equation

HRID 351852 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=4[O:24][CH3:25])[C:13](=[O:14])[C:4]=2[CH:3]=1)=[C:9]([C:26]([NH:28][OH:29])=[NH:27])[N:8]=[CH:7]3.[O-2].[Mg+2].[CH:34]1([C:37](Cl)=O)[CH2:36][CH2:35]1>O1CCOCC1>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=4[O:24][CH3:25])[C:13](=[O:14])[C:4]=2[CH:3]=1)=[C:9]([C:26]1[N:27]=[C:37]([CH:34]2[CH2:36][CH2:35]2)[O:29][N:28]=1)[N:8]=[CH:7]3

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 6850729Magnesium monoxideHCID 178490756HCID 178490756, compound

Product 1

HCID 22713464HCID 22713464, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8-Chloro-5-(2,4-dimethoxy-benzyl)-N-hydroxy-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxamidine (1.9 g, 4.3 mmol), magnesiumoxide (0.156 g, 3.9 mmol), and cyclopropanecarbonyl chloride (0.5 mL, 5.3 mmol) were refluxed in dioxane overnight. Dioxane was evaporated and the residue dissolved in DMF (20 mL) and refluxed for 1 h. DMF was evaporated and the residue extracted with CH2Cl2 and water. The product crystallized upon concentration of the organic layer and dilution with ethyl acetate. One obtained a white solid (0.8 g, 39%). mp 198-205° C. m/z 492 (MH+).

Workup

  1. customDioxane was evaporated
  2. dissolutionthe residue dissolved in DMF (20 mL)
  3. temperaturerefluxed for 1 h
  4. customDMF was evaporated
  5. extractionthe residue extracted with CH2Cl2 and water
  6. customThe product crystallized upon concentration of the organic layer and dilution with ethyl acetate

Sources & evidence

ORD record
ord-cb652cb9b667406bbf28299dfbdc7fd9
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

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