Water → 7-Chloroacetylimidazo[5,1-b]thiazole

HRID 1839316Notes

Reaction equation

HRID 1839316 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[S:10]1[CH:14]=[CH:13][N:12]2[CH:15]=[N:16][CH:17]=[C:11]12.O>ClCCCl>[Cl:1][CH2:2][C:3]([C:17]1[N:16]=[CH:15][N:12]2[CH:13]=[CH:14][S:10][C:11]=12)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21262404Imidazo[5,1-b]thiazole

Product 1

HCID 234493337-Chloroacetylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Chloroacetyl chloride (5.97 ml) was added to a solution of 12.5 g of aluminum chloride in 40 ml of 1,2-dichloroethane. The mixture was stirred at room temperature for 20 min. A solution of 1.93 g of imidazo[5,1-b]thiazole in 20 ml of 1,2-dichloroethane was added thereto. The mixture was heated under reflux for 2 hr. Water was added thereto, followed by extraction with dichloromethane. The organic layers were combined together. The combined organic layers were washed with a dilute aqueous sodium hydroxide solution and saturated brine in that order. The solvent was removed by distillation. Isopropyl ether was added to the residue. The resultant powder was collected by filtration to obtain the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. extractionfollowed by extraction with dichloromethane
  4. washThe combined organic layers were washed with a dilute aqueous sodium hydroxide solution and saturated brine in that order
  5. customThe solvent was removed by distillation
  6. additionIsopropyl ether was added to the residue
  7. filtrationThe resultant powder was collected by filtration

Sources & evidence

ORD record
ord-4f5d5f2db3fb4a84878cf71c7032a9d8
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

Loading…