Hydrochloric Acid → HCID 10445094, compound

HRID 728129Notes

Reaction equation

HRID 728129 reaction equation
[CH3:1][NH:2][C:3](=[S:18])[NH:4][C:5]1[CH:17]=[CH:16][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1.BrBr.Cl.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O1CCCC1.C(OCC)(=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][C:8]1[CH:16]=[CH:17][C:5]2[N:4]=[C:3]([NH:2][CH3:1])[S:18][C:6]=2[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24408BromineHCID 10377776HCID 10377776, compound

Product 1

HCID 10445094HCID 10445094, compoundYield 12.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[4-(3-methylthioureido)benzyl]pyridine (4.0 g) in chloroform (80 ml) was dropwise added the solution of bromine (0.9 ml) in chloroform (5 ml) at ambient temperature and the mixture was heated under reflux for 2.5 hours. The reaction mixture was added to 10% hydrochloric acid (60 ml) and the mixture was heated under reflux for 20 minutes. To the separated aqeuous layer was added a solution of ethyl acetate and tetrahydrofuran and the resultant solution was adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography eluting with a mixture of chloroform and ethyl acetate (4:1 V/V). The eluted fractions containing desired product were evaporated to give 6-[(2-pyridyl)methyl]-2-methylaminobenzothiazole (0.48 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 20 minutes
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe crude product obtained by concentration
  8. customwas purified by silica gel column chromatography
  9. washeluting with a mixture of chloroform and ethyl acetate (4:1 V/V)
  10. additionThe eluted fractions containing desired product
  11. customwere evaporated

Sources & evidence

ORD record
ord-78fafe8452fa4007a61976a41892cc20
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

Loading…