Dichloromethane → HCID 178423695, compound

HRID 728159Notes

Reaction equation

HRID 728159 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][N:16]4[C:23]=3[CH3:24])[CH:8]=[CH:7][C:5]=2[N:6]=1.B(Br)(Br)Br.[Cl:29]CCl>>[ClH:29].[ClH:29].[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][N:16]4[C:23]=3[CH3:24])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 10359782HCID 10359782, compound

Product 1

HCID 178423695HCID 178423695, compound

Procedure

The mixture of 2-amino-6-[2-(7-methoxy-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzothiazole (2.3 g) and boron tribromide (6.4 ml) in dichloromethane (115 ml) was stirred for 20 hours at ambient temperature and the solvent was evaporated in vacuo. A mixture of obtained residue and water was adjusted to pH 7.5 with 20% potassium carbonate aqueous solution and resulting precipitate was collected by filtration and dried. The residue was purified by alumina column chromatography eluting with a solution of chloroform and methanol (4:1, V/V). The fractions containing object compound were concentrated in vacuo. To a mixture of obtained residue and ethanol (3 ml) was added conc. hydrochloric acid (0.2 ml) and the mixture was stirred for 30 minutes at ambient temperature. The resulting precipitate was collected by filtration and dried to give 2-amino-6-[2-(7-hydroxy-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzothiazole dihydrochloride (0.22 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionA mixture of obtained residue and water
  3. customresulting precipitate
  4. filtrationwas collected by filtration
  5. customdried
  6. customThe residue was purified by alumina column chromatography
  7. washeluting with a solution of chloroform and methanol (4:1, V/V)
  8. additionThe fractions containing object compound
  9. concentrationwere concentrated in vacuo
  10. additionTo a mixture of obtained residue and ethanol (3 ml)
  11. additionwas added conc. hydrochloric acid (0.2 ml)
  12. stirringthe mixture was stirred for 30 minutes at ambient temperature
  13. filtrationThe resulting precipitate was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-83232dffe10048849f6750632fb2c603
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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