Propylamine → 2-(5-Methylthien-2-yl)-N-propylimidazo[2,1-b]-benzothiazole-3-acetamide

HRID 36909Notes

Reaction equation

HRID 36909 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[N:8]=[C:9]3[N:13]([C:14]=2[CH2:15][C:16](O)=[O:17])[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]3)=[CH:4][CH:3]=1.[CH2:23]([NH2:26])[CH2:24][CH3:25]>O1CCCC1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[N:8]=[C:9]3[N:13]([C:14]=2[CH2:15][C:16]([NH:26][CH2:23][CH2:24][CH3:25])=[O:17])[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 152338102-(5-Methylthien-2-yl)imidazo[2,1-b]benzothiazole-3-acetic acid

Product 1

HCID 540062702-(5-Methylthien-2-yl)-N-propylimidazo[2,1-b]-benzothiazole-3-acetamideYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.6 g (0.005 mole) of 2-(5-methylthien-2-yl)imidazo[2,1-b]-benzothiazole-3-acetic acid are treated, at room temperature, with 0.85 g (0.005 mole) of N,N'-carbonyldiimidazole in 30 ml of anhydrous tetrahydrofuran for 3 h 30 min. A solution composed of 3 g (0.05 mole) of propylamine in 10 ml of anhydrous tetrahydrofuran is added and the mixture is stirred for 4 h at room temperature. The solvent is evaporated under reduced pressure, the compound is collected by filtration, it is washed with water up to neutral pH, then with ethanol and finally with ethyl ether and it is purified by recrystallization from methanol. 1.1 g of a light yellow solid are obtained. Melting point: 204°-206° C.

Workup

  1. additionis added
  2. customThe solvent is evaporated under reduced pressure
  3. filtrationthe compound is collected by filtration, it
  4. washis washed with water up to neutral pH
  5. customwith ethanol and finally with ethyl ether and it is purified by recrystallization from methanol

Sources & evidence

ORD record
ord-913f9c7fd66746ae845bdb59c546d7cd
Source dataset
uspto-grants-1995_05
Patent number
US05418248

Reaction notes

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