Triethylamine → HCID 18983825, compound

HRID 1440469Notes

Reaction equation

HRID 1440469 reaction equation
Br.[C:2]1([C:8]2[N:9]=[C:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=[CH:12][N:11]3[CH:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([N:24](CC)CC)C.ClS(N=C=O)(=O)=O>C(#N)C>[C:22]([C:21]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]2=[N:9][C:8]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 67768891Ethyl 2-phenyl-imidazo[1,2-a]pyridine-8-carboxylate hydrogen bromide

Product 1

HCID 18983825HCID 18983825, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl 2-phenyl-imidazo[1,2-a]pyridine-8-carboxylate hydrogen bromide (1.96 g, 5.35 m mol), and triethylamine (0.55 g, 5.44 m mol) were added to acetonitrile (20 ml). To this solution was dropwise added a solution of chlorosulfonylisocyanate (ClSO2NCO) (0.8 ml, 9.19 m mol) in acetonitrile (5 ml) at an inner temperature of 0°-20° C. Then, the mixture was allowed to react at room temperature for an hour. After completion of the reaction, the mixture was concentrated under reduced pressure. The resulting concentrate to which water was added was extracted with dichloromethane, and the extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to give the object compound (1.06 g, yield 67.9%) as crystals. m.p. 87°-89° C.

Workup

  1. customto react at room temperature for an hour
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. concentrationThe resulting concentrate to which water
  5. additionwas added
  6. extractionwas extracted with dichloromethane
  7. washthe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-9149e09e3713462eaaa386625a1c5a6c
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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