Thionyl Chloride → HCID 21873927, compound

HRID 723417Notes

Reaction equation

HRID 723417 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]2[C:10]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=[CH:7][N:6]2[C:18]=1[CH3:19].S(Cl)([Cl:22])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:22][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=[CH:7][N:6]2[C:18]=1[CH3:19]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 21873962HCID 21873962, compound

Product 1

HCID 21873927HCID 21873927, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 13 g of 2-hydroxymethyl-3-methyl-8-pivaloylaminoimidazo[1,2-a]pyridine in 500 ml of dry dichloromethane is added dropwise a solution of 6.5 g thionyl chloride in 50 ml dry dichloromethane at 0–5° C. to give a clear yellow solution. After 2 h the reaction mixture is hydrolysed by adding 200 ml saturated sodium bicarbonate solution under cooling. The resulting mixture is transferred to a separatory funnel and shaken vigorously. The organic layer is separated, washed with water and dried over anhydrous sodium sulfate. The solvent is removed in vacuo to give 12.7 g (92%) of the title compound (m.p. 168° C.).

Workup

  1. customto give a clear yellow solution
  2. temperatureunder cooling
  3. customThe resulting mixture is transferred to a separatory funnel
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-dcd3c9324aec4b53b4c79ba7a25b6370
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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