Thionyl Chloride → HCID 14155692, compound

HRID 1382759Notes

Reaction equation

HRID 1382759 reaction equation
S(Cl)(Cl)=O.O[CH:6]([C:12]1[N:16]2[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][CH3:30])=[CH:24][CH:23]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8].C(S([O-])=O)O.[Na+]>C(Cl)Cl>[CH3:11][N:9]([CH3:10])[C:7](=[O:8])[CH2:6][C:12]1[N:16]2[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][CH3:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 23689980Sodium Formaldehyde SulfoxylateHCID 54316816HCID 54316816, compound

Product 1

HCID 14155692HCID 14155692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8.5 ml of thionyl chloride are added dropwise to 1.5 g (4.2×10-3 mol) of α-hydroxy-N,N-dimethyl-6-methyl-2-[4-(methoxymethyl)phenyl]imidazo[1,2-a]pyridine-3-acetamide (IX) dissolved in 85 ml of dry methylene chloride. The mixture is left stirred for 15 h at room temperature and evaporated to dryness, the residue is taken up with pentane, crystallized and dried under vacuum. A white solid is obtained which is dissolved in 120 ml of methylene chloride, 1.9 g (1.2×10-2 mol, 3 eq) of Rongalite are added and the mixture is left stirred for 4 h at room temperature. The mixture is then filtered and the filtrate washed with bicarbonate water and then with water to neutral pH, dried and evaporated. The product is purified by chromatography and crystallized in ether.

Workup

  1. waitThe mixture is left
  2. customevaporated to dryness
  3. customcrystallized
  4. customdried under vacuum
  5. customA white solid is obtained which
  6. waitthe mixture is left
  7. stirringstirred for 4 h at room temperature
  8. filtrationThe mixture is then filtered
  9. washthe filtrate washed with bicarbonate water
  10. dry with materialwith water to neutral pH, dried
  11. customevaporated
  12. customThe product is purified by chromatography
  13. customcrystallized in ether

Sources & evidence

ORD record
ord-b252ea100f4649798fdcf7613e56ec23
Source dataset
uspto-grants-1989_02
Patent number
US04808594

Reaction notes

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