Tripropylamine → HCID 18983840, compound

HRID 1440471Notes

Reaction equation

HRID 1440471 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]2[C:15]=1[S:16]([OH:19])(=O)=[O:17].C(N(CCC)CCC)CC.P(Cl)(Cl)([Cl:32])=O>C(#N)C>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]2[C:15]=1[S:16]([Cl:32])(=[O:19])=[O:17]

Participants

5

Reactant 3

HCID 7616TripropylamineHCID 24813Phosphorus oxychlorideHCID 18983812HCID 18983812, compound

Product 1

HCID 18983840HCID 18983840, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-methyl-3-sulfo-imidazo[1,2-a]pyridine-8-carboxylate (1.7 g) and tri-n-propylamine (2.6 g) were added to acetonitrile (17 ml). Phosphorus oxychloride (1.1 ml) was added to the mixture, keeping the inner temperature to 50°-60° C. Then, the mixture was allowed to react at the same temperature for an hour. After completion of the reaction, the mixture was concentrated under reduced pressure, and water was added to the residue. The precipitated crystals were collected by filtration, washed with water and dried to obtain ethyl 2-methyl-3-chlorosulfonyl-imidazo[1,2-a]-pyridine-8-carboxylate (1.2 g, yield 66.3%) as crystals of m.p. 182°-183° C.

Workup

  1. customto 50°-60° C
  2. customto react at the same temperature for an hour
  3. customAfter completion of the reaction
  4. concentrationthe mixture was concentrated under reduced pressure, and water
  5. additionwas added to the residue
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-0b2d5f04754747abb5ccbbd1bba045c3
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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