Acetic Acid → HCID 12369479, compound

HRID 258868Notes

Reaction equation

HRID 258868 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[C:10]1[S:11][CH:12]=[C:13]([CH2:15]Cl)[N:14]=1.C1N2CN3CN(C2)CN1C3.C(O)(=[O:29])C>C(Cl)(Cl)Cl.O>[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[C:10]1[S:11][CH:12]=[C:13]([CH:15]=[O:29])[N:14]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4101Hexamethylenetetramine2×HCID 12369474HCID 12369474, compound

Product 1

HCID 12369479HCID 12369479, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

2-(1-methyl-5-nitroimidazol-2-yl)-4-chloromethylthiazole (0.2 mole) and hexamine (0.3 mole) in chloroform (400 ml.) were stirred and boiled under reflux for 20 hours. The solid product was collected, washed in chloroform and dried to yield 2-(1-methyl-5-nitroimidazol-2-yl)-4-thiazolylmethyl hexaminium chloride. The latter (0.078 mole) was dissolved in water (150 ml.) and glacial acetic acid (150 ml.). Hexamine (10 g.) was added and the solution refluxed for 11/2 hours. The solution was evaporated to 50 ml. and water (200 ml.) added. The precipitate was collected and dried to give 2-(1-methyl-5-nitro-imidazol-2-yl)thiazole-4-carboxaldehyde, m.p. 180°-182° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe solid product was collected
  3. washwashed in chloroform
  4. customdried
  5. customto yield 2-(1-methyl-5-nitroimidazol-2-yl)-4-thiazolylmethyl hexaminium chloride
  6. temperaturethe solution refluxed for 11/2 hours
  7. customThe solution was evaporated to 50 ml
  8. additionand water (200 ml.) added
  9. customThe precipitate was collected
  10. customdried

Sources & evidence

ORD record
ord-b21f5a513b0944578f71c490e9d89d64
Source dataset
uspto-grants-1977_07
Patent number
US04035390

Reaction notes

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