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

HRID 1730185

Reaction equation

HRID 1730185 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., 0.0155 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 22 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-99b246c9bdc8479c9a0236635a3792a8
Source dataset
uspto-grants-1976_11
Patent number
US03991200

Linked notes

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