Carbon Disulfide → HCID 20228703, compound

HRID 1731359Notes

Reaction equation

HRID 1731359 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([NH2:20])[CH:14]=3)[N:12]=[C:6]2[CH:5]=1.Cl.Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+].[C:36](=S)=[S:37]>O.C(O)C>[CH3:3][C:4]1[CH:9]=[CH:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]4[O:19][C:36]([S:37][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=5)=[N:20][C:15]=4[CH:14]=3)[N:12]=[C:6]2[CH:5]=1

Participants

8

Reactant 5

HCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 157504012-Amino-4-(7-methylimidazo[1,2-a]pyridin-2-yl)phenol

Product 1

HCID 20228703HCID 20228703, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of potassium hydroxide (0.67 g) and carbondisulfide (0.91 g) in a mixture of water (1.5 ml) and ethanol (50 ml) was added 7-methyl-2-(3-amino-4-hydroxyphenyl)imidazo[1,2-a]pyridine (2.4 g) and the mixture was refluxed for 5 hours under stirring. To the reaction mixture was added a solution of 2-chloromethylpyridine hydrochloride (4.9 g) and potassium carbonate (3.8 g) in a mixture of water (5 ml) and ethanol (20 ml) at ambient temperature and the resultant mixture was stirred for 3 hours. The precipitate collected by filtration, was suspended in a mixture of water, tetrahydrofuran and ethyl acetate and the mixture was adjusted to pH 11 with 20% potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo to afford a crystalline residue, which was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 5-(7-methylimidazo[1,2-a]pyridin-2-yl)-2-(pyridin-2-ylmethylthio)benzoxazole (1.6 g). mp. 184°-185° C. (dec.).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. filtrationThe precipitate collected by filtration
  3. additionwas suspended in a mixture of water, tetrahydrofuran and ethyl acetate
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto afford a crystalline residue, which
  8. customwas recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-9888b9e87ac34ddf8c3ae2608d6da52a
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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