1-Methylimidazole → HCID 21828743, compound

HRID 558037Notes

Reaction equation

HRID 558037 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[CH2:7]([Li])[CH2:8][CH2:9]C.CN(C)C(=O)C.COC(OC)N(C)C.[NH2:26][NH2:27]>C(O)C.O1CCCC1>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[NH:27][N:26]=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 13901-MethylimidazoleHCID 9321HydrazineHCID 31374DimethylacetamideHCID 78373Dimethylformamide dimethyl acetalHCID 178418339Butyllithium

Product 1

HCID 21828743HCID 21828743, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 100 ml two-necked reaction flask is dried under vacuum and baked by fire and then cooled by nitrogen gas flow. 50 ml of anhydrous tetrahydrofuran and 1-Methylimidazole (10 mmol, 0.8 ml) are added. n-Butyl lithium agent (12 mmol, 4.8 ml) is slowly added at −78° C. After the reaction has been taken place for 15 minutes, N,N-Dimethylacetamide (12 mmole, 1.12 ml) is added into the flask to react at the room temperature. Extraction with ether and water is carried out and the organic layer is concentrated to obtain a liquid product. The yield is 83%. The obtained product is then reacted with N,N-Dimethylformamide dimethyl acetal (12.45 mmol, 1.65 ml) without any solvent at 100° C. for 10 hrs. Extraction with methylene chloride and water is carried out and the organic layer is concentrated to obtain solids. The yield is 93%. The obtained product is dissolved in ethanol and then added with hydrazine (28.95 mmol, 1.40 ml). The reaction is carried out for 3 hrs at 90° C. The reaction solution is concentrated and extracted by methylene chloride and water. The organic layer is concentrated and separated by n-hexane and ethyl acetate through chromatographic column. The product mip is thus obtained and the yield is 71%. 1H NMR (400 MHz, CD2Cl2): δ 7.63 (d, 1 H, J=2 Hz), 7.09 (br, 1 H), 6.98 (s, 1 H), 6.71 (br, 1 H), 3.928 (s, 3 H).

Workup

  1. customA 100 ml two-necked reaction flask is dried under vacuum and baked by fire
  2. temperaturecooled by nitrogen gas flow
  3. customfor 15 minutes
  4. customto react at the room temperature
  5. extractionExtraction with ether and water
  6. concentrationthe organic layer is concentrated
  7. customto obtain a liquid product
  8. extractionExtraction with methylene chloride and water
  9. concentrationthe organic layer is concentrated
  10. customto obtain solids
  11. concentrationThe reaction solution is concentrated
  12. extractionextracted by methylene chloride and water
  13. concentrationThe organic layer is concentrated
  14. customseparated by n-hexane and ethyl acetate through chromatographic column
  15. customThe product mip is thus obtained

Sources & evidence

ORD record
ord-2e810f48da2a45eab99b0268a0ce1bda
Source dataset
uspto-grants-2011_11
Patent number
US08062767B2

Reaction notes

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