Hydrochloric Acid → HCID 9997860, compound

HRID 728139Notes

Reaction equation

HRID 728139 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]3[N:14]=[C:15]([NH2:17])[S:16][C:12]=3[CH:11]=2)=[N:6][CH:7]=1.[Br:20]Br.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:19]=[C:18]([Br:20])[C:13]3[N:14]=[C:15]([NH2:17])[S:16][C:12]=3[CH:11]=2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24408BromineHCID 10038732HCID 10038732, compound

Product 1

HCID 9997860HCID 9997860, compoundYield 51.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-[2-(5-methyl-2-pyridyl)ethyl]-2-aminobenzothiazole (1.35 g) in acetic acid (15 ml) was dropwise added a solution of bromine (0.8 g) in acetic acid (2 ml) at 20° to 22° C. under stirring and the resultant mixture was stirred at ambient temperature for 5 hours. The reaction mixture was poured into a mixture of water and ethyl acetate and the mixture was acidified to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 8.0 with aqueous 20% potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 6-[2-(5-methyl-2-pyridyl)ethyl]-2-amino-4-bromobenzothiazole (0.9 g).

Workup

  1. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo and residue
  5. customwas recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-2f7a1dc7d7204fe595460f6d71c6b4a9
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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