N,N-Dimethyl-1,3-propanediamine → 2-[2-(3-Dimethylaminopropylamino)-5-thiadiazolyl]-1-methyl-5-nitroimidazole

HRID 462224

Reaction equation

HRID 462224 reaction equation
Cl[N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1.[CH3:16][N:17]([CH3:22])[CH2:18][CH2:19][CH2:20][NH2:21].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH3:16][N:17]([CH3:22])[CH2:18][CH2:19][CH2:20][NH:21][N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 516892Sodium BicarbonateHCID 213908012-(2-Chloro-5-thiadiazolyl)-1-methyl-5-nitroimidazole

Product 1

HCID 213908562-[2-(3-Dimethylaminopropylamino)-5-thiadiazolyl]-1-methyl-5-nitroimidazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture consisting of 3.8 gm., 0.0l55 mole of 2-(2-chloro- 5-thiadiazolyl)-1-methyl-5-nitroimidazole, prepared as in Example 16 2.5 gm., 0.029 mole of 3-dimethylaminopropylamine, 2.1 gm. 0.025 mole, of sodium bicarbonate and 100 ml. of benzene is refluxed for twenty-two hours. The reaction mixture is cooled to room temperature, washed with aqueous sodium bicarbonate and sodium chloride solutions. Cooling to 5° C. gives a crystalline precipitate which is collected and recrystallized from benzene to give the pure compound melting at 153°-154° C. More product is obtained from the mother liquors to give an overall yield of 3.0 gm.

Workup

  1. washwashed with aqueous sodium bicarbonate and sodium chloride solutions
  2. temperatureCooling to 5° C.
  3. customgives a crystalline precipitate which
  4. customis collected
  5. customrecrystallized from benzene

Sources & evidence

ORD record
ord-cdd44bd3a9914425890b4ab15887956a
Source dataset
uspto-grants-1977_12
Patent number
US04065567

Linked notes

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