Chloroacetaldehyde → HCID 16735617, compound

HRID 910212Notes

Reaction equation

HRID 910212 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17](=[S:19])[NH2:18])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[CH2:20](N(CC)CC)[CH3:21].ClCC=O.O>C(O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:17]4[S:19][CH:20]=[CH:21][N:18]=4)=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 962WaterHCID 8471TriethylamineHCID 16735147HCID 16735147, compound

Product 1

HCID 16735617HCID 16735617, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(6-Iodoimidazo[1,2-a]pyridin-2-yl)-1-benzenecarbothioamide (249 mg) was dissolved in ethanol (10 mL). Triethylamine (91 μL) and chloroacetaldehyde (155 μL) were added to the solution, and the mixture was refluxed for 18 hours. Water was added to the reaction mixture, followed by extraction with dichloromethane-methanol. The solvent was evaporated, and the residue was purified through silica gel column chromatography (dichloromethane:methanol=100:5), followed by concentration under reduced pressure, to thereby yield the title compound (103 mg).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. extractionfollowed by extraction with dichloromethane-methanol
  3. customThe solvent was evaporated
  4. customthe residue was purified through silica gel column chromatography (dichloromethane:methanol=100:5)
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-730375c343bc410f9e6f4f984f84b6bd
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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