Dimethylformamide → HCID 18922493, compound

HRID 1290005Notes

Reaction equation

HRID 1290005 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[C:11]1([C:17]2[N:24]3[C:20]([S:21][CH:22]=[CH:23]3)=[CH:19][N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[C:11]1([C:17]2[N:24]3[C:20]([S:21][CH:22]=[CH:23]3)=[C:19]([CH:9]=[O:10])[N:18]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 18922518HCID 18922518, compound

Product 1

HCID 18922493HCID 18922493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus oxychloride (0.6 mL, 6.44 mmol) was added to DMF (2.5 mL) over 5 minutes with cooling in an ice-bath. 5-Phenylimidazo-[5,1-b]-thiazole (500 mg, 2.5 mmol) was added, and the mixture was kept overnight at room temperature. The thick solid that had formed was slurried in methylene chloride and stirred for 30 minutes with 10% aqueous sodium carbonate solution. The organic layer was separated, washed with saturated brine solution and evaporated. The title compound was obtained after flash chromatography eluting with 20% acetone in hexane.

Workup

  1. temperaturewith cooling in an ice-bath
  2. customThe thick solid that had formed
  3. customThe organic layer was separated
  4. washwashed with saturated brine solution
  5. customevaporated

Sources & evidence

ORD record
ord-b6d85f81cacd40e99bb999e653f057d2
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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