Benzylamine → 5-Iodo-N-(phenylmethyl)imidazo[2,1-b]-1,3,4-thiadiazol-2-amine

HRID 1942320Notes

Reaction equation

HRID 1942320 reaction equation
[I:1][C:2]1[N:9]2[C:5]([S:6][C:7](S(C)=O)=[N:8]2)=[N:4][CH:3]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[CH2:13]([NH:20][C:7]1[S:6][C:5]2=[N:4][CH:3]=[C:2]([I:1])[N:9]2[N:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 671090085-Iodo-2-(methanesulfinyl)imidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 582853975-Iodo-N-(phenylmethyl)imidazo[2,1-b]-1,3,4-thiadiazol-2-amineYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Iodo-2-methanesulfinyl-imidazo[2,1-b][1,3,4]thiadiazole (500.00 mg; 1.60 mmol; 1.00 eq.) was dissolved in dichloromethane (1.60 ml) and benzylamine (622.18 μl; 4.79 mmol; 3.00 eq.) was added. Then, the reaction was refluxed overnight. The reaction was concentrated in vacuo. Then, 5 ml of isopropanol were added and the suspended solution was heated under reflux for 15 min. The mixture was allowed to cool to room temperature and then cooled to 0° C. After 15 min at 0° C., the solid was filtered and washed with isopropanol to give a white solid. The solid was dried at 60° C. for 1 h to give 460.2 mg of the desired product.

Workup

  1. temperatureThen, the reaction was refluxed overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. additionThen, 5 ml of isopropanol were added
  4. temperaturethe suspended solution was heated
  5. temperatureunder reflux for 15 min
  6. temperaturecooled to 0° C
  7. filtrationthe solid was filtered
  8. washwashed with isopropanol
  9. customto give a white solid
  10. customThe solid was dried at 60° C. for 1 h

Sources & evidence

ORD record
ord-5812b330eef54daf9d7f5983b9732bf7
Source dataset
uspto-grants-2013_03
Patent number
US08389554B2

Reaction notes

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