1-Methyl-2-imidazolecarboxaldehyde → HCID 89420968, compound

HRID 246201Notes

Reaction equation

HRID 246201 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[CH3:9][C:10]([S:13]([NH2:15])=[O:14])([CH3:12])[CH3:11]>ClCCl>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1/[CH:7]=[N:15]/[S:13]([C:10]([CH3:12])([CH3:11])[CH3:9])=[O:14]

Participants

4

Reactant 2

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 89420968HCID 89420968, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

In a 25 mL vial, cupric sulfate (1.96 g, 12.3 mmol), 1-methyl-1H-imidazole-2-carbaldehyde (450 mg, 4.09 mmol) and 2-methylpropane-2-sulfinamide (594 mg, 4.9 mmol) were combined with dichloromethane (2 ml) to give a light blue suspension. The reaction mixture was stirred at 25° C. for 15 h then filtered through Celite. The reaction mixture was filtered again through silica gel eluting with ethyl acetate. The crude reaction mixture was concentrated in vacuo to provide 670 mg (76%) of 2-methyl-propane-2-sulfinic acid 1-(1-methyl-1H-imidazol-2-yl)-meth-(E)-ylideneamide as an oil. 1H NMR (300 MHz, CDCl3): δ 8.62 (s, 1H), 7.27 (bs, 1H), 7.08 (bs, 1H), 4.02 (s, 1H), 1.26 (s, 9H).

Workup

  1. customto give a light blue suspension
  2. filtrationthen filtered through Celite
  3. filtrationThe reaction mixture was filtered again through silica gel eluting with ethyl acetate
  4. customThe crude reaction mixture
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-ce804fb0d3a144c1acba6c8f7b12f4fe
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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