Potassium Carbonate → HCID 15171533, compound

HRID 728140Notes

Reaction equation

HRID 728140 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:16]4[N:17]=[C:18]([NH2:20])[S:19][C:15]=4[CH:14]=3)[N:10]=[C:4]2[CH:3]=1.[BrH:23].[NH+]1C=CC=CC=1.Br.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(OCC)C.C(OCC)(=O)C.O>[Br:23][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]2=[N:10][C:9]=1[CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[C:18]([NH2:20])[S:19][C:15]=2[CH:14]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 9972556HCID 9972556, compoundHCID 21226041Pyridinium hydrobromideHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 15171533HCID 15171533, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-aminobenzothiazole (0.4 g), pyridinium hydrobromide perbromide (0.5 g) and 25% hydrogen bromide-acetic acid (0.1 ml) in acetic acid (4 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated to give a residue, which was triturarted with a solution of ethyl acetate and diethyl ether to give a precipitate. The precipitate was collected by filtration and dried to give 6-[2-(3-bromo-7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-aminobenzothiazole (0.38 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customto give a residue, which
  5. customto give a precipitate
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-00d839f0cf1a469c93bfbf8f561736a2
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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