Hexamethylenetetramine → HCID 12038723, compound

HRID 1978351Notes

Reaction equation

HRID 1978351 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:17]1N2CN3CN(C2)CN1C3.C(OCC)(=O)C>C(O)(=O)C>[N:1]1[CH:2]=[C:3]2[N:4]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=13)[S:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17]2

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 8857Ethyl AcetateHCID 9816120HCID 9816120, compound

Product 1

HCID 12038723HCID 12038723, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl (imidazo[1,2-a]pyridin-5-ylthio)acetate (11.8 g) in acetic acid (120 ml) was added hexamethylenetetramine (14.0 g) and the mixture was reacted at 90° C. for 10 hours. After this reaction mixture was allowed to cool, ethyl acetate (360 ml) was added and the mixture was washed with water. The organic layer was neutralized with 30% aqueous solution of sodium hydroxide under ice-cooling and washed again with water. The organic layer was concentrated and n-hexane (100 ml) was added to the crystalline residue, followed by 1 hour of stirring at room temperature. The crystals were collected by filtration and dried to provide the title compound (9.6 g, 78%).

Workup

  1. customthe mixture was reacted at 90° C. for 10 hours
  2. temperatureto cool
  3. washthe mixture was washed with water
  4. temperaturecooling
  5. washwashed again with water
  6. concentrationThe organic layer was concentrated
  7. additionn-hexane (100 ml) was added to the crystalline residue
  8. filtrationThe crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-bfcdec4ef27449819d87716ad88f963e
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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