Acetic Acid → HCID 12369479, compound

HRID 1729632Notes

Reaction equation

HRID 1729632 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-01345d6d3d8c46f9a3e8353a366a4303
Source dataset
uspto-grants-1976_11
Patent number
US03989690

Reaction notes

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