Dichloromethane → HCID 9857808, compound

HRID 2183611Notes

Reaction equation

HRID 2183611 reaction equation
C(=O)([O-])O.[Na+].Br.[S:7]1[CH:11]=[CH:10][C:9]2[C:12]([C:16]3[N:17]4[CH2:24][CH2:23][N:22]=[C:18]4[S:19][C:20]=3[CH3:21])=[CH:13][CH:14]=[CH:15][C:8]1=2.[Cl:25]CCl>O>[ClH:25].[S:7]1[CH:11]=[CH:10][C:9]2[C:12]([C:16]3[N:17]4[CH2:24][CH2:23][N:22]=[C:18]4[S:19][C:20]=3[CH3:21])=[CH:13][CH:14]=[CH:15][C:8]1=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 10291641HCID 10291641, compound

Product 1

HCID 9857808HCID 9857808, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium hydrogencarbonate (17.84 g) in water (300 ml) was added at 0° C. to a suspension of 3-(benzo[b]thiophen-4-yl)-2-methyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (15.0 g) in dichloromethane (300 ml), the mixture was stirred vigorously for 25 minutes, then the organic phase was separated, dried (Na2SO4), and the solvent was removed in vacuo. The residue was dissolved in ethanol (100 ml), the solution was cooled to 0° C., and 2M ethereal hydrogen chloride solution (28 ml) was added. The mixture was stirred for 20 minutes then the solvent was removed in vacuo. The residue was triturated with a 1:1 mixture of ethanol and ether (50 ml), then the resulting solid was collected by filtration and recrystallised from propan-2-ol to give 3-(benzo[b]thiophen-4-yl)-2-methyl-5,6-dihydroimidazo[2,1-b]thiazole hydrochloride (6.3 g) as a colourless solid, m.p. 235-238° C. Concentration of the liquor yielded a second crop of 3-(benzo[b]thiophen-4-yl)-2-methyl-5,6-dihydroimidazo[2,1-b]thiazole hydrochloride (2.7 g) as a colourless solid, m.p. 234-237° C.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethanol (100 ml)
  5. addition2M ethereal hydrogen chloride solution (28 ml) was added
  6. stirringThe mixture was stirred for 20 minutes
  7. customthe solvent was removed in vacuo
  8. customThe residue was triturated with a 1:1 mixture of ethanol and ether (50 ml)
  9. filtrationthe resulting solid was collected by filtration
  10. customrecrystallised from propan-2-ol

Sources & evidence

ORD record
ord-b3361241325c44188fc1b09f79fe0acd
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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