1-Methylimidazole → HCID 178423384, compound

HRID 558038Notes

Reaction equation

HRID 558038 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].CN(C)C(=O)C.COC(OC)(N(C)C)C.[NH2:27][NH2:28]>C(O)C.O1CCCC1>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[NH:28][N:27]=[C:9]([CH3:10])[CH:8]=1

Participants

8

Reactant 5

HCID 13901-MethylimidazoleHCID 9321HydrazineHCID 31374DimethylacetamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 178418339Butyllithium

Product 1

HCID 178423384HCID 178423384, 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-Dimethylacetamide dimethyl acetal (12.45 mmol, 1.82 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 90%. The obtained product is dissolved in ethanol and then added with hydrazine (28.01 mmol, 1.36 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 mimp is thus obtained and the yield is 75%. 1H NMR (400 MHz, CD2Cl2): δ 7.04 (s, 1 H), 6.94 (s, 1 H), 6.74 (s, 1 H), 3.91 (s, 3 H), 2.34 (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 mimp is thus obtained

Sources & evidence

ORD record
ord-7ca7ccdba6114c48a634b3db06d76bf7
Source dataset
uspto-grants-2011_11
Patent number
US08062767B2

Reaction notes

Loading…